You’ve played this person a bunch of times before, but you always lose somehow. You’re going to be playing them again and don’t know what to do. You feel like you’re a contender, but can never actually eek out the win.
So what do you do? Do what Rocky would do in Rocky II. Although he lost his bout to Creed in Rocky I, he comes back to win the next time around. He trains harder than Creed, for starters. So train harder. Condition yourself to be better than your opponent and last longer. He also develops a weapon and a way to win. So if you don’t have one, build yourself a shot that you can consistently hit aggressively (forehand crosscourt, or backhand down the line?).
Why have you lost in the past? Did they beat you or did you beat yourself? If they beat you, then you must get better and re-evaluate your strategy. If you beat yourself (by hitting errors), then you must simply get better.
In re-evaluating your strategy, re-evaluate your opponent. What are their strengths and weaknesses? What do you think or assume are their strengths and weaknesses? For instance, often times you will feel like your opponent has a weaker backhand because they never rip winners with their backhand. So you hit it to that side whenever you can. But it could be the case that they hit a ton of errors on their forehand, and it only appears to be a strong shot because they occasionally hit a good one with a lot of flash. So think about where they generate most of their errors and try to make them hit those shots over and over.
Don’t play their game and don’t play to their rhythm. If they like playing slowly, try to play faster in between points, and vice-versa. Rocky didn’t try to dance around and out-jab Creed, which was Creed’s game, Rocky had to get to the inside and go for the body blows.
A lot of times your opponent, having won before in the past, will expect to win easily without too much effort. They’ll be complacent and let you win points and games you probably shouldn’t deserve. You have to capitalize on this. At some point they will wake up, and think ‘hey this game is way too close. I’m starting to get worried!’ and then they will buckle down to really focus on every single point. If at that point when they are absolutely determined to win every point, you cannot afford to be complacent yourself and satisfied that the match is as close as it is. You can’t let them catch you sleeping mentally. Treat each point as though it were crucial for the match. Want the win more than they do. If you think they’re waking up and starting to really try hard (sometimes people yell at themselves or noticeably try to get pumped up). This is a great time to hit the ball neutral down the middle of the court. Make them try to force a play – hit an angle from the middle – it’s a very low percentage shot! You are reducing your chances of errors, and making them feel like they aren’t playing their usual game. They’ll press to try and win from a sub-optimal position, and either come up with an error, or put you in a good position to win the point. Maybe they’ll hit an unlikely winner, sure. But you will have played the statistically superior play and over time it will pay off.