It is like Chris says in all English's with = on the same team/side against means in completion with.
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'playing with' is correct, but it is more common to hear or read 'playing against'.
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In the US and Canada, "playing with" is not used to mean team X against team Y.
"Playing with" means as part of the team as in "Tom Smith has been traded and is now playing with (for) team X."
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