Tournament of Losers — Megan Derr

All Rath wants is a quiet, peaceful life. Unfortunately, his father brings him too much trouble -- and too many debts to pay -- for that to ever be possible. When the local crime lord drags Rath out of bed and tells him he has three days to pay his father's latest debt, Rath doesn't know what to do. There's no way to come up with so much money in so little time. Then a friend poses an idea just ridiculous enough to work: enter the Tournament of Losers, where every seventy-five years, peasants compete for the chance to marry into the noble and royal houses. All competitors are given a stipend to live on for the duration of the tournament -- funds enough to cover his father's debt. All he has to do is win the first few rounds, collect his stipend, and then it's back to trying to live a quiet life...