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Editor’s note: If you had to play one match for your life, you’d be strongly advised to seek the strategic and tactical advice of Brad Gilbert. As a player, he reached a career-high ranking of No. 4 in the world in 1989. As a coach, he’s greatly helped such greats as Andre Agassi, Andy Roddick, and Coco Gauff earn Grand Slam singles titles. Gilbert’s best-selling book, Winning Ugly, offers tons of insights into what it takes to dissect opponents and figure out how to beat them. This kind of tactical engagement is rare – and yet deeply meaningful if a player seeks to generate better results. For this story, we asked Brad to address a complicated question: How do you beat someone you’ve never beaten?
1. The Thinking Player’s Mindset
“I know this is difficult, but no matter how many times in a row you’ve lost to someone, you’ve got to think, ‘this is match one.’ Then you’ve got to think about what you need to do tactically – both what you want to make happen and what you don’t want to happen from your opponent’s end. For example, if he’s better at you in crosscourt backhand exchanges, then think…
