There are two ways you can go about this achievement (and all similar ones).
Natural GameplayIf you are going for the completion, you will need to play through the entire career. This gives you 10 opportunities at each achievement, assuming you win every Grand Slam. I unlocked three of the four male achievements during one career playthrough, so it is possible.
Start a New CareerIf you have finished the career, and just want a specific achievement, start a new career. Now skip to the event of your choice (US Open is Event 12). Upon entering the tournament, you should press X to show the Full Tree. Hopefully, the player you want to face is in the same half (6 wins needed) or quarter (5 wins needed) as you. If they are on the other side, you will need 7 wins.
You will now need to win every game and hope that you and your opponent (Evert) face at some point during the tournament. If they lose a game, quit back to the main menu, and start a new career.
NotesOnce a tournament is started, the results are set in stone. This means that reloading a previous save (by duplicating your save game on to another device) will not work.
Please either comment below or send me a Personal Message if you have any comments or improvements.