Those comments explain why you lost. 1. He hit safely by dinking stuff back. He knows the first rule of tennis: don't miss. You violated that rule by missing. 2. Your solutions (come to net, hit behind him) are isolated shots, not patterns of play. 3. You can't make him put up anything since he knows you're willing to do that and make UEs. He has no reason to put up anything to score points, you're doing it for him. Here's a potential two or three-shot solution if he has a weak backhand: 1. In crosscourt BH exchange hit deep crosscourt without much pace...just get the ball deep and as wide as possible with decent margin for error. Your low pace will make the ball bounce below the net forcing him to pop it up over the net for a no pace dinker/floater. 2. If he's really a safety minded dinker his shot will be cross- to mid court and not very deep...start moving there while your shot is outbound. 3. He's now deep on his ad side, you're maybe on your ad side to mid-court inside the baseline with a floating duck. If you're really as good as you say you are then the deuce court is wide open and you have control of the middle and are in a stable hitting position as the ball floats up off a soft bounce. You can sense his movement and based on his move and the ball's characteristics you can: - pause, let him commit, and hit crosscourt behind him as he moves to the middle - drop shot short on his deuce side - if the ball bounces high hit flat down the line with pace meaning at a 90-degree angle to the baseline which takes away time while reducing your chance of making an error by hitting wide accidentally. In all three cases he's scrambling to get to the ball. And in all three cases, since you know the shot you're taking, you can start moving to position after striking the ball. If you: - hit behind him then setup crosscourt on the ad side, his highest percentage shot, and you're already roughly there - if you drop shotted then close the net a little bit crosscourt of the ball - if you hit DTL with pace then move crosscourt to the deuce side between the baseline and service line In all three cases his return should be weak and, if he's a disciplined dinker then he'll go for the high percentage shot and you're already be in position for a put away. That's a three shot play that sets you up for a put-away and exploits his no-pace, big safety margin hitting and weak backhand. And your shots need not be mighty monster topspin shots. Just solid, easy shots will do the trick. Finally, if he's hitting with such low pace and you're really that good once inside the baseline you should be taking some of those shots out of the air with volleys or swing-volleys giving him even less time to teleport. For example, in the play above the third shot is probably a volley opportunity for a put-away. Even a pusher can't violate the laws of physics by teleporting. I learned this because, after playing a notorious dinker in our area, I was determined to not suffer through three-hour dink fests by dinking back. In that dinker match he hurt himself diving for a drop shot and so I was spared the pain of a three hour dink fest when he retired. But that experience and watching a female friend engage in epic three-hour dink fests when she ran into other dinkers made me determined to develop weapons and strategies to avoid that boring nonsense. My wife and I also hit for fun and she's the perfect dinker-bot for 3.0/3.5 training. As a low-mid level player it's easy to go for too much against her and give up just enough points to lose. Her only "weapon" is a wicked angled CC BH that's impossible to reach from the baseline. Knowing that it's easy to exploit her low pace, safe shots by using shot selection and court position to safely run her around. In fact, she's even developed her BH as a result of our play. For a while I would hit to her BH knowing where her shot was going and I'd close the net and hit an easy DTL winner. She then made me do drills with her so she could prefect a DTL winner off her BH. Now I'm hosed if I hit CC to her BH without pace or depth: she either hits a sharp angle CC which is nearly impossible to get or she goes safely DTL with a Djoker-like precision since it's low-pace mid-level tennis. I can't be in two places at once and so she just hits after I commit. Now I must hit harder CC to her BH to apply pressure so she must return CC or risk missing on the low percentage DTL shot against a high pace shot. Tennis: it's a study in Darwinism!