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Winning Ugly

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He's been called the best in the world at the mental game of tennis. Brad Gilbert's strokes may not be pretty, but looks aren't everything. He has beaten the Tour's biggest names -- all by playing his "ugly" game.

Now, in Winning Ugly Gilbert teaches recreational players how to win more often without necessarily even changing their strokes. The key to success, he says, is to become a better thinking player -- to recognize, analyze, and capitalize. That means outthinking opponents before, during, and after a match; forcing him or her to play your game. Gilbert's unconventional advice includes:

* How to identify the seven "Hidden Ad Points," and what to do when they come up

* Six reasons why you should never serve first

* How to beat a Lefty, a Retriever, a Serve-Volley player, and other troublesome opponents

* How to keep a lead, or stop a match from slipping away

* How to handle psyching and gamesmanship

Winning Ugly is an invaluable combat manual for the court, and its tips include "some real gems," according to Tennis magazine. Ultimately, Winning Ugly will help you beat players who have been beating you.

274 pages, Paperback

First published January 1, 1993

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About the author

Brad Gilbert

11 books11 followers
Brad Gilbert is an American former professional tennis player, influential coach, author, and commentator whose analytical approach to the sport has shaped the careers of numerous top athletes. Raised in California, he developed a reputation early on for his competitive spirit and strategic clarity rather than relying on raw power, a distinction that defined both his playing style and later his coaching philosophy. Turning professional in the early 1980s, he accumulated 20 ATP singles titles and achieved a career-high ranking of world No. 4, marking him as one of the most consistently formidable players of his era. His success was built on intelligent point construction, mental discipline, and an ability to exploit opponents’ weaknesses, qualities that earned him respect throughout the tennis community. After stepping away from full-time competition, Gilbert became one of the sport’s most sought-after coaches. He worked with Andre Agassi during a career resurgence that resulted in multiple major titles and a return to the No. 1 ranking. He later coached Andy Roddick to a US Open championship and contributed to the development of several other notable players, including Andy Murray, Kei Nishikori, and Coco Gauff. His coaching is distinguished by practical problem-solving, psychological resilience, and an emphasis on winning through adaptability rather than style alone. Gilbert also built a prominent media and literary career. As a longtime ESPN analyst, he provides commentary grounded in clear tactical breakdowns, often emphasizing what players need to adjust in real time. His books, including Winning Ugly and I’ve Got Your Back, articulate his belief that understanding the mental and strategic layers of the game is as crucial as physical training. Widely recognized for his contributions, Gilbert has been inducted into multiple halls of fame and continues to lecture, consult, and teach within the sport. His legacy extends beyond match results, influencing generations of players and coaches who embrace the idea that success often depends not on who hits the best shots, but on who thinks the smartest, prepares the hardest, and competes with the greatest resilience.

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Displaying 1 - 30 of 296 reviews
Profile Image for Peter.
61 reviews4 followers
February 17, 2023
I just finished this ugly tennis book, haha.

I’ve played tennis for about 20 years now and seem to love it more than ever. I started to play competitively again earlier this year and picked up this book off my shelf for a refresher.

When I played as a junior, I believe I was pretty good but a mental numbnuts on court. I never prepared correctly by sleeping, dieting, developing a plan, being aware of my weapons and weaknesses, or anything else. To my first high school coach, this was all probably extremely obvious, and she let me borrow her copy of this book either Freshman or Sophomore year. I poked through a few chapters, but about 15 years later I’ve finally read the full thing (I never gave it back to her: another reason I was a high school numbnuts).

First, would it have benefitted me to read the whole thing while I was a junior player? Probably not, but that would have been my own fault. I was pretty aware that sleeping well, analyzing your opponent, and adjusting your game were all keys to victory, but I don’t think I could’ve convinced myself to actually do any of those at the time. When I was younger, I was totally aloof towards anything that mattered, which is recognizable now as arrogance or stubbornness.

Do I think I got anything out of reading it now? Kind of. Yeah, I’ll say more or less. I think I’m a better student about everything now. One hump is that the book reads like an ancient text of tennis, reported in a dated, pre-internet voice that's equivalent to home remedies like keeping nickels in your pocket to avoid the flu. It doesn’t help that Gilbert is a cornball the whole way through. I think starting chapters with quotes from his mom about how he was a precocious chore dodger are pretty cringe. When he sagely declared the secret energy drink to be “water”, I rolled my eyes a little. DRM is a frequent acronym that means “Don’t Rush Me”, and he offers all kinds of eccentric ways one might put this into action during a match: touch your strings, tie your shoes, move your towel from one side of the court to the other, go touch a rock in the corner after every point. Very "grandma's home remedy" tennis right there.

But that last kind of advice is also where the dated cornballness kind of starts to appeal to me. There’s definitely a dedication to just doing what works because it seems to work. Even if it’s not science or scripture, he’s tried these things and for some reason they bring results. One of my favorite bits of advice is keeping snacks in your bag, and when Brad recommends a candy bar he mentions that some people might say not to eat that much sugar since you’ll crash, but if that happens just to eat another, “who knows”. These imperfect pieces of advice appeal to me maybe just sentimentally. He sounds like coaches I had growing up, and maybe they’re borrowing their voices from books and coaches like this.

Right now, it’s really easy to learn tennis strategy and technique off YouTube, and unfortunately these channels are pressured to provide quick fixes and attractive visual branding in order to maintain and grow an audience. I see all kinds of bizarro advice based on buzzwords about learning a “modern forehand” or applying “kinetic chain” principles. The videos that have the most views often have somebody swinging a racket with an arbitrary red circle around their wrist or racket and the words “DO THIS” or “STOP DOING THIS” and then they talk long enough to get YouTube ad revenue and plug old videos. I at least think this book is better than those videos, and the current trend of horrible thumbnails even makes me warm up to the horrendously ugly book cover image.

So I like this book as an extended lesson that you need to revisit and think about time and again. It’s definitely more useful than watching Youtube videos, and it gives advice that is probably worth the money from a professional coach but nobody would really want to pay for. The basic message is that most players will go out to the court brain dead, and that you can do that or you can try to come out and apply your mind to something else besides your personal mechanics. Brad spends 200 pages trying to prove his message that 10% of the time you’re going to get your ass kicked no matter what, 10% of the time you’re going to kick their ass no matter what, and 80% of the time the match is up for grabs and that the only thing that matters in competition is the score at the end of the day. I think it’s encouraging. I can see it making tennis more fun, freshening up your mindset a bit, and maybe actually getting a few more wins.

I’ll say a big bonus are anecdotes about old pros too, what Brad would tinker with during a match against Agassi, Sampras, and the rest of the gang. It’s notable that he talks very highly about Jim Courier’s game, who had won 4 majors in the 2 years before the book came out, but then never won one again afterwards. Not everything from 1994 tennis can age as well as the rest of his advice.
Profile Image for Sid.
84 reviews4 followers
July 4, 2017
As an avid tennis player, Brad Gilbert's book has many helpful pointers. His ideas of preparation, focus, execution and adaptation can help a player of any level. I thoroughly enjoyed Brad's own personal accounts of battles with some of the game's greatest players of the time. It was remarkable to see how Brad's powers of observation helped coach Agassi and turnaround his career that was stuck in a rut, to helping him climb back to greatness! I'm happy to recommend this book to anyone for it's instructional and entertainment value.
Profile Image for Jorge Castillo.
43 reviews1 follower
February 4, 2020
After reading on "Open" about the amazing results Andre Agassi had once he added Brad Gilbert on his team it was clear for me that the next book I needed to read was Winning Ugly.
In his book, Gilbert, teaches all the "not so talented" tennis players out there that you don´t need to be a prodigy to win tennis matches. You just need to know how to exploit your strengths, minimize risks and attack your opponent's weaknesses.
If you are looking forward to increase your percentage of winning matches, this book is definitely for you.
Profile Image for Susan.
586 reviews2 followers
February 23, 2020
4.5 stars. Excellent book even though it was originally written in the early 90s and references tennis stars from that era (Agassi, Connors and McEnroe to name a couple). Lots of timeless advice about how to mentally approach the game if you want to win...and most of it is applicable at all levels of play. Highly recommend!
Profile Image for Phil.
461 reviews
September 4, 2024
Lots of technical advice for the tennis player, whether aspiring to professional greatness or simply wanting to crush the local club competition. A bit dated now in terms of the player references, but the basic tactics and psychological insights remain largely the same as today.

Full disclosure: I do NOT play tennis, nor pickleball. So why listen to this one? Because I actually enjoy watching tennis competition on TV, especially the major tournaments such as the US Open currently underway. What fascinates me is the ongoing psychological battle going on inside each player's head, one that plays out in a constant up and down manner throughout each swing of the racket and each point won or lost.

When it comes to the majors (Australian Open, French Open, Wimbledon, and US Open) most pros are playing not just for a paycheck but also for the personal, lasting glory that comes from achieving success on the largest sporting stage in front of a global audience. You know they are going to give their all.

Further, they are alone on the court (except when playing doubles) with no teammate to pick up the slack as needed. There's no huddle after each play to discuss strategy. At best, there's a quick comment or sign from a coach, but other than that the player is stuck inside their own head and grappling silently with each micro-issue as it evolves.

Watching that process unfold is absolutely fascinating to me. Why does a player up 6-0 in a first set go on to lose the match? Why does a player spiral out of control after a double fault? Why are some players rarely bothered by a mistake? It's all about the head game.

For that aspect of tennis, the author offers an abundance of fascinating insights that will take the spectator's appreciation of the game to a much higher level. Many of his tips are applicable to other sports and even non-sporting activity.
Profile Image for Rob.
Author 6 books30 followers
September 30, 2016
I remember the furore when this review came out and thought I'd turn to it having taken up tennis again recently and steadily gotten involved in more and more competitive matches. It's a bit like a training course in that one or two pearls of wisdom are to be derived but overall, it's a little disappointing and tame, even if the central tenet, that mental toughness can overcome a multitude of technical drawbacks is only too true.

Gilbert loves winding up the likes of John McEnroe and is a real caricature of a brash Californian but I found quite a lot of it obvious - as a 47 year old with a weak backhand and a tendency to commit unforced errors, I've already had to think deeply about how to beat opponents of greater youth and ability and so much was familiar. The stuff on gamesmanship is actually pretty tepid too - save for the section on deliberate throwing toys out of prams to gain an advantage and to influence an umpire and the section about dodgy line calls. The most unappealing thing about the book is Gilbert's tendency to list his achievements according to the prize money on offer at the various events - topical given I read this during the week of Sam Allardyce's sacking as England manager.

Cycling could probably do with a similar treatment mind.
Profile Image for Rebecca.
107 reviews2 followers
April 24, 2007
Not exactly a typical read for me and the book cover's as ugly as the title. Brad Gilbert's shaded mug and the yellow type face can make you feel a bit queasy after lunch. But should you be a competitive type who'd like to do better at tennis (on an amateur level) this is the book for you. And I love the insights and gossip into how he beat some of the greats and got McEnroe into a rage (not difficult I guess).
10 reviews
May 7, 2017
Brad Gilbert's book contains simple but excellent advice for club players and tips from the pros that can make a difference in tournament matches. I found useful reminders of basic equipment, warm-ups, strategies like never serving first, play at 65% but consistently at first, the importance of the first two games, what to do when you're behind and in front, how to use psychological strategies and guard against those used by the opponent. I was distracted by, and skimmed through, his frequent reports of his own tournaments with former greats; many of them seemed to be just cathartic.

I would rather have had just the tips with brief examples. But it's his book :)
Profile Image for Arne-Jan.
342 reviews5 followers
May 28, 2025
Toen ik in 2005 in Rotterdam kwam wonen had ik ook mijn voetbal moeten opzeggen. Dat was één van de zwaarste aspecten aan vertrekken. Maar goed, Rotterdam had natuurlijk ook voldoende mooie clubs. Van V.O.C. had ik weleens gehoord en hield ik in gedachten. De eerste periode in Rotterdam was ik echter niet bepaald bezig met sporten. Werken was vaak van 7.30-19.30. Eerlijk gezegd was dat ook wel een beetje het sfeertje bij het Big-4 kantoor waar ik zat: work hard, play hard. Dat laatste bestond dan uit de Frank-borrel op vrijdag, eerst op telkens wisselende geheime locaties die pas kort van tevoren bekend werden gemaakt aan de bezoekers, later in de Cruise Terminal. Je kunt je voorstellen dat het weekend vooral diende om bij te komen, maar ik genoot met volle teugen van het bruisende leven in 010.

In 2007 verhuisde ik, een paar straten verderop. Mijn eerste appartement gekocht! Ik kwam pal naast de tennisbaan te wonen. Omdat ik ook net een nieuwe werkgever had en dus wat meer tijd had, besloot ik me aan te melden. Geen voetbal dus, maar tennis. Een keuze die ik ook al eens maakte toen ik een jaar of vijftien was. Ik mocht komen kennismaken met een team dat twee nieuwe leden zocht. Dat klikte. En hoe. Geweldige gasten die ook direct mijn netwerk weer wat verbreedden. Twee jaar geleden heeft de laatste van die oorspronkelijke groep afscheid genomen. Blessures, padel, verhuizingen; lastig om een team bij elkaar te houden. Inmiddels staat er een heel nieuwe team bij een andere club. Een klasse beter ook dan het oude team, maar ik mis de magic van die oude groep nog weleens. Iets meer karakters, gekke acties en heroïsche overwinningen en schandelijke verliespartijen waar ik nu nog weleens gillend van wakker word. En dan elke competitiedag ’s avonds de tennisclub sluiten.

Het lijfboek van Mark was Winning Ugly. Mark was een hel voor iedere tegenstander: de meest bizarre forehand slice- en kapballen, fantastische volleys en de ene na de andere bal die over het hek vloog. En dan een attitude van heb-ik-jou-daar. Als hij half zo goed had kunnen tennissen als ontregelen... Op dit niveau werkte het wel regelmatig: singles van drie uur tegen veel betere spelers waar de gezichten steeds meer van betrokken. Inmiddels zit ik zelf in een fase waarin het tennissen me minder makkelijk afgaat door allerlei blessures en een gebrek aan motivatie. Ik herinnerde me Winning Ugly. Ik vroeg het aan de Sint. Ik had het een paar weken geleden uit, het móest en zou uit zijn voor de competitie weer begon. Dat lukte. In mijn hoofd nam ik de smerige trucs en mind games in bed nog eens door de avond voor de eerste wedstrijd. Die zaterdag verloor ik 6-0 6-2, de week erna zelfs een dubbele bagel. Sinds week 3 ben ik weer geblesseerd. Toch wil ik Winning Ugly aanraden: mooie verhalen over het tijdperk waarin ik zelf opgroeide met échte sterren als McEnroe, Edberg, Becker en natuurlijk Krajicek. Ik sluit ook niet uit dat de tips van Gilbert voor een ander wel werken. Zelf ga ik eerst maar weer eens proberen op te krabbelen en de bal op een normale manier over het net te krijgen.
Profile Image for Rosie Seagraves.
18 reviews
October 14, 2023
To me, an adult beginner, this book felt like a long, friendly conversation about all the different aspects of the game that a lesson or clinic isn't going to cover. I have a feeling I'll be coming back to it time and again. I understand the critiques about how it's dated, but the proof is still in the pudding. Go Coco!!!
Profile Image for Maria.
165 reviews
November 3, 2024
Für Tennisspieler ein absolutes Muss. Ich konnte viel für mein eigenes Training mitnehmen. 🙏🏼
2 reviews
October 31, 2017
Winning Ugly is the best tennis book out there. It taught great strategies before, during, and after matches. The book taught me lots of great things which actually improved my game. It taught me the accurate stretches before a match. This book was an informational genre book. Usually, books from this genre are boring and I never read them. This one was the best one so far it taught me in-game strategies that I used to improve my game and won more matches. If you want to improve your tennis game then I would definitely recommend this book.
Profile Image for Martí Sala Perramon.
286 reviews10 followers
May 5, 2019
It has been a brilliant reading I have really enjoy it. It has been the best tennis book I have read.
It was written during the 90’s but it isn’t old fashion it really fits the tennis essence.
It talks about tennis strategy the mental and psychological part of this sport and how to win in all types of situations even though the match isn’t going the way you will like.
Some of the advices you can apply them in other life situations.
Profile Image for Haruka Kosugi.
8 reviews1 follower
July 18, 2021
As a huge fan of Andre Agassi and his autobiography Open, I was interested in the ideas from a coach that was a major contributor to Agassi’s assurgent tennis career from talented bad boy to bonafide champion. This isn’t the most engaging or personal book, but it isn’t meant to be. If any of his tips help you win 5% more of the points that you play, it’s worth the time.
Profile Image for Jonathan.
19 reviews2 followers
November 18, 2024
This book was practically written about me - certainly for me. My technique is anything but orthodox; I serve with my right but rally with my left. I've trademarked a two-handed tomahawk-chop volley at the net. All while using my mental game and athleticism (albeit fading with age) to beat guys that have much better technique. And this book has equipped me with a whole arsenal of strategy, tactics, and tips that produced immediate results and consistent improvement. Combine this book with Gallwey's Inner Game of Tennis & you'll be a force to be reckoned with at any age or skill level.
Profile Image for Kristen Brennan.
72 reviews1 follower
June 17, 2024
As a person who loves to play tennis on the recreational level, I thought this book had a lot to offer in terms of strategy, lessons learned and great advice for competing at your best and coming out on top no matter what level you are. I enjoyed hearing his real life experiences during matches, and his progression from competing at the professional level to coaching a tennis legend was pretty cool. I enjoyed this one a lot and will definitely read it again during the tennis season.
Profile Image for J. E..
137 reviews1 follower
July 1, 2025
Reading this coincided with the start of the tennis grass court season, my daughter asking for advice on her serve and me picking up my racket for the first time in 10 years! It made this an even more significant read as I study the game for myself. It's more tactics than technique but mixes professional tennis with amateur using Gilbert's own player experiences playing against some of the greats of the 80s. I certainly enjoyed all aspects.
Profile Image for Stephen.
1 review
Read
August 30, 2024
Hi Brad. Thanks to your book, I'm now one step closer climbing up the ladder at my local tennis club in Oslo Norway
62 reviews
December 23, 2024
10/10 couldn't have been better for my tennis and also a little about life. Which I think is the best case for instructional sports books
Profile Image for Derk.
16 reviews
March 5, 2025
Solid book on mental tennis strategy. Did not get a lot of the 1990 references to top players at the time, but had a lot of helpful tactics to think about during match play. Makes me want to go pro.
Profile Image for Ethan Jordt.
136 reviews
September 10, 2024
Overall some really good gems of info. To me it wasn't the most interesting read though
Profile Image for Danile Queen.
79 reviews1 follower
January 21, 2025
well its cold and i dont want to pay for indoor tennis so instead im studying theory in the wintertime
also my flight back got delayed and i missed my connection so now im waiting for the redeye and i am first on the waiting list fingers crossed!! 🤞
Profile Image for Murad.
26 reviews1 follower
October 23, 2024
almost bageled my tennis partner after reading this
20 reviews
July 3, 2021
If you're a tennis player and if you remember watching the greats of the 80s and 90s (Lendl, McEnroe, Connors, Chang, Becker, Agassi, Sampras,...) on the tube, you're going to breeze through Gilbert's book.
Alternating between on the one hand practical advice on how to improve your match play not by working on your strokes, but on the analysis of strengths and weaknesses and how to make these work to your advantage, and on the other hand anecdotes of how his own approach fared and improved against the iconic players of the game, Gilbert provides a great story on how preparation, a plan, alertness and resolve can decide a match rather than mere physicality and pure skill.
Profile Image for Brian Matthews.
37 reviews
March 5, 2024
Former professional player and coach of Andre Aggasi, Andy Murray, and Coco Gauff's book on the mental aspect of tennis. Wish I had read this a while ago but have picked up on some of the strategies outlined through playing in high school and tournaments. Biggest takeaway is to think on the court. Very easy to become braindead idiot once stepping foot on the court. Using your brain during a match allows you to see opportunities (e.g. hidden AD points) that most other players will fail to recognize and apply your strengths against the opp's weaknesses.
Profile Image for Morgan Lyons.
313 reviews15 followers
February 25, 2018
All I knew about Brad Gilbert before reading this book is that it's always really annoyed me the way he calls Roger Federer "buddy" in all his post-match on-court interviews. After finishing the book it STILL really annoys me (mostly because there's nothing to suggest that he and Roger are in fact buddies at all, and wouldn't we all love to pretend we're good pals with Federer, but why does this guy think he actually IS just because he does a 5-minute interview with him twice a year?!) Moving on...
The book itself was quite good. At first I thought I might not enjoy it because it's somewhat dated; after all, Gilbert played in the era of Connors, McEnroe, and Lendl, so naturally he draws from his experiences during that time and with those players. Sampras and Agassi were after his time, to say nothing of the current greats like Rafa, Djoker, or Brad's good buddy Roger.
But as I got deeper into the book, I realized that the techniques and insights Gilbert shares span more than a single generation of tennis; they're universal principles that can be applied just as effectively by players today as they could have been by players 30 years ago. Gilbert's own path through the world of tennis reveals just how true this is, because while he never made it past the quarterfinals of a grand slam tournament during his career as a player, he used the tactics taught in this book to coach Agassi to 6 of his 8 slams, Roddick to his 1 (and only) U.S. Open, and help move Andy Murray firmly into the top 5. Now if I can just find a time machine and start applying all this good stuff 15 years ago, maybe I can make the tour too.
Fortunately, this book has helpful advice even for those of us who WON'T ever play tennis at a professional level, and I would absolutely recommend it to anyone who wants to strengthen their mental (and by extension, all-around) tennis game.
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