Technique
- Where is his crossover point (in terms of where does he switch from a forehand to a backhand and vice versa). Is it different for backspin and topspin balls? When in doubt, does he use the backhand or forehand more?
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Does he recover to a neutral ready position, or does he prefer to recover to one side most of the time? Or does he recover to the same side that the last ball was hit from (i.e. if his last shot was a backhand, he gets ready for another backhand)?
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Footwork - is he better going from side to side or in and out? Is he fast or slow? Can he be caught out wide to the forehand? Does he move better in one direction (i.e. running around the backhand) than another (going wide to the forehand)?
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Timing - does he prefer to play his main strokes as the ball is rising, at the top of the bounce, or on the way down? You may be able to make him play more strokes from where he is not comfortable.
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Is his technique suspect in any way? For example, does his grip give him a better forehand at the expense of his backhand? Or make him stronger against topspin but weaker against backspin?
Temperament
- Does his expression and/or body language show what he is feeling? If not, are there any other signs of his situation, such as dropping the ball on the table before serving, wiping his hands on the table, or more deep breaths before serving?
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Does he pretend to be feeling something else? An opponent who does this may be trying to play mind games with his opponent, such as John McEnroe's temper tantrums in tennis, which were often designed to upset the opponent's rhythm and concentration.
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Does he tend to give up when he falls behind in a match? If you can get a lead you may be able to get him to stop trying.
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Does he ease up when ahead? Don't give up against this opponent and you may be able to make a good comeback due to his lack of effort.
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Have you ever seen him lose his temper or saw anyone else get under his skin? If so, why did it happen? This can tell you a lot about what he does or doesn't like, and may be useful if you want to distract him from the game. (Note - I'm not saying be rude to your opponent - but if you know he hates delays, taking a bit of extra time now and then when toweling, or making him wait that bit longer before serving can be legitimate tactics. There is sometimes a fine line between gamesmanship and bad sportsmanship. Try to stay on the right side if you can. ;) )
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Does he like to play to the crowd? Does he like to hit big winners so the crowd can applaud? If so, make sure that you acknowledge the great shots that he hits, but try to make it difficult for him so that he misses two for every one that he gets on. You might be able to keep him trying to hit wonderful winners and not noticing all the mistakes he is making.
Equipment
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If possible, get a look at your opponent's bat well before your match, or ask reliable sources for any information on what he uses. At the very least try to watch him play so you can tell if he is using some type of pimples or antispin. You want to get as much advance warning on what type of rubbers you are going to face.
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Make sure you check out his bat before you start playing the match. You want to see for yourself exactly what he is using - don't take anyone else's word for it (or his!).
The Overall Package
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Don't get so caught up in your opponent's individual strengths and weaknesses that you forget his overall game. His footwork may appear jerky and awkward, but that won't help you if that jerky footwork moves him around the court fast enough to hit the ball. His backhand may look terrible, but if it goes on consistently forget about the technique and look at the result.
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Speaking of results, it's what he can do during the matches that counts, not how good he looks in the warm up.
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Ask other players who have faced your opponent for their ideas and impressions about how he plays, and what worked well for them and what didn't. They may not be 100% accurate or totally applicable to your style of play, but they will give you a good starting point for your own plans.
Video Analysis
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Try to get your opponent on tape if you can, against as many opponents as possible. Study the tape as often as you need to in order to identify the points mentioned above. Video analysis is great since you get to check and see what really happened during a match, rather than what you thought just happened.
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Tape your own match against your opponent - again, it's very helpful to be able to concentrate on your match at the time, and then be able to go back later to analyze all the points you missed.
Conclusion
I hope you find these thoughts helpful when you are getting ready to check out your next important opponent. I just hope I don't find you standing behind me with a notebook or video camera!