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I find this expression strange because it's clearly widely used, but seems sort of "unofficial", the "official" version, meaning the one described in dictionaries and grammar books, being playing games with, not on.

Both expressions seem to be current and valid, according to Google Books. I'm just not entirely clear on the context and the usage.

My understanding is that playing games with implies some sort of tricky, mischievous behavior, which may or may not be intentionally malicious, like office politics or standing someone up on a date ("Jane didn't show up...again. Is she playing games with me?"), while playing games on implies a form of studied deception. ("The ad said that the comic book was in mint condition but there are barely noticeable tears... are they trying to play a game on me?")

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up vote 2 down vote accepted

This is what the Oxford Online dict says

play on: exploit (a weak or vulnerable point in someone): he played on his opponent’s nerves
play with: treat inconsiderately for one’s own amusement: she likes to play with people’s emotions

And another reference from there shows us that to play games on someone does imply some sort of trick which can be (or not) malicious (technically). But its mostly used in a non-positive sense.

So to ans your question, both play game on and play game with can suggest the malicious nature, depending on what context its being used in. E.g:
"Quit playing games (with me) and come to the point man!"
"He is playing a game on her to like him" -Studied deception
"He will never marry her! He is just playing games with her (for sex)" - suggesting studied deception again.

play games on is less commonly used, and even lesser commonly used in British Eng compared to US, as seen in the Google Ngrams below: enter image description here enter image description here

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I don't think "Play games on" is commonly used. I have not been able to find a reference for it that fits the meaning you give it in your example. "Play on" is clear and "play games with" is also clear. Maybe it's just not used in my part of the world/country/region. –  Kristina Lopez Mar 22 '13 at 18:21
    
I added a relative Ngram. –  camelbrush Mar 22 '13 at 19:59
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I agree with @KristinaLopez. I think "play a trick on" is a much more commonly used phrase to convey that meaning. –  Carolyn Mar 22 '13 at 20:29
    
@camelbrush, fyi - I ran the Ngrams also and the hits on "play games on" are not the same context as the OP's question. I couldn't find one example from the Ngrams data. –  Kristina Lopez Mar 22 '13 at 21:08
    
I agree playing games on is not common, but I do agree with the original poster about 'playing games on' suggesting malicious intent. –  camelbrush Mar 22 '13 at 21:13
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