I played most of this game on the lower difficulties and didn't seem to get any of these. I managed to get it using Play Now and setting the difficulty to Legend. It seems that you get more chances for the ball to clip the tape and go over when you are using approach shots and half volleys. These are shots made around the service box, which is halfway from the baseline to the net. Using this method, I got the achievement in one match.
If you are having trouble, you can also try aiming for the middle of the net. The net in tennis is shortest there, and the elasticity can help to catapult the ball over the tape. The alternate shot input, the RS, can also help. Pull the RS back to ready, then push forward to release. I got a few using this method as well.