The two sites where I have uploaded entries to PhotoShop contests are Fark.com and Cracked.com.
The big difference between the two is that the Fark contests usually have a source image to work with. Cracked contests are always theme or topic-based, and they usually require research.

These 5 stand out because Cracked actually pays money for winners. These won me actual money. Unlike everything else I've ever done, just for the fun of it.

Cracked Photoplasty - 12/27/2016 - $25 15 Resolutions And How You'll Rationalize Breaking Them
Fourth place

Cracked Photoplasty - 12/20/2015 - $25 15 In-Universe Facts That Will Change How You See Star Wars
Eigth place

Cracked Photoplasty - 6/15/2015 - 20 Things We Suspect Customer Service Staff Are Really Doing
Seventh place

Cracked Photoplasty - 6/5/2015 - 21 Movies & TV Shows If They Honored The Source Material
Fifth place

Cracked Macro Contest - 6/1/2015 - $100 20 Ridiculous Coincidences That Saved Movie Heroes
First place

 

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