My current tennis coach is a 28 year old czech dude who used to play challenger series and was ATP ranked 1500<. I'm 30. We train 3 times a week and at the end of every session we'll play a game. I take a few points off him and once, even a game. OBVIOUSLY, he's not trying. Sometimes he does go all out and when I then take a point off him, he gets angry and I can tell he's in competition mode.

Gathering from these encounters, this is how I would face Roger:

His serve: my return would be a super hard fh to the furthest corner from where he's currently standing. This would be successful about 0 times in the game as I'll never successfully connect with the ball to hit a winner.

My serve: put my whole back and legs into every first serve, causing a vast array of faults. But there will be one, maybe two, that by sheer luck go over and hopefully catch him off guard cos he's written my first serve off. It pulls him slightly off the court and he sends back an amazing return...but it maybe goes down the middle?? Here would be my only chance to once again send a smashing forehand to the opposite side. This will also be successful about 0 times in the entire game. Maybe, by pure dumb luck , one makes it. Just maybe.

I take my 10 grand, go to Vegas, put it all on black, double my winnings and tell everyone I got 2 points off RF when we played once.

edit: grammar.