Rather than asking a coach or a teacher what I should do during a tennis match, my modus operandi was to go down a quick checklist.
1) Can this person put enough balls in play to beat me? I usually assessed this in the warm up. As a kid I played tennis in Minnesota and in the early rounds, the answer to this question was often "no". If the answer was "no" I simply hit balls over the net and waited for the opponent to miss. If, "yes", on to...
2) Does this person have an obvious weakness? Again, obvious weaknesses show up in the five minute warm up. Usually this will be a backhand. Forehand weaknesses are usually more subtle. Volley and overhead weakness, movement trouble, short second serves, etc are often pretty obvious. If I found a weakness, I exploited it. If I couldn't find a weakness, I'd move on to ...
3) Can I find a weakness? This is tougher than spotting an obvious weakness. To do this you have to move the ball around more during play. You have to mix up velocities and spins. Perhaps the backhand is sound, but not so sound on the run or high or low. Modern forehands often break down under pressure or when the player is on the run to their dominant side. Usually what I'll do is just move the person around the court and observe the shots I receive in reply. If I can't find any weaknesses...
4) I'll begin to try different game plans to see if I can win points. In my case that was generally to serve and volley. Hitting winning shots is easier to do from the front of the court than from the rear of the court. If you're a good defender, maybe you draw your opponent forward so you can pass or lob them. Maybe you just grind them down, forcing them to beat you with winning shots from bad court positions.
In the course of going down this checklist, hopefully I found some way to win the match. Finding a weakness and being able to exploit it to win a match are two different things. It may be that your opponent can't do something as well as something else, but you can't get to the weakness, or worse, the weakness is still better than your strength.
There is no magic bullet for every opponent. But going down some sort of checklist will help you find ways to win more matches.
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