I had run a contest for the top 3 entries to each win $133.33 (total of $400). When it came time to award the winners, I realized that you can NOT split up a contest prize among different people.
This was an issue - since I had three separate people who deserved the prize. Thankfully, Freelancer support was able to work with me so that we could treat everyone fairly. I appreciate the time and support from them.