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Brad Gilbert and Andre Agassi played 8 ATP matches before Gilbert retired as a tennis player and later became Agassi's coach.

Amelie Mauresmo and Marion Bartoli played 5 WTA matches before Mauresmo retired as a tennis player and later became Bartoli's coach.

I am sure there are more examples like these in the world of tennis, but cannot think of any. Any ideas?

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Sampras and Paul Annacone played once. Agassi and Darren Cahill also played twice during the overlap of their careers. I would imagine some of the younger coaches (like Roger Rasheed for example) might have played some of the players they've coached.

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I just checked for Roger Rasheed, he is not one of the examples, hence I'll remove the part mentioning him in your answer. – user0810 Jul 5 '14 at 12:02

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