The episode title is a play on the idiom "may the best man win", which is said in the spirit of sportsmanship.
The kitten Fluttershy offers to Rainbow Dash resembles the cats from Hasbro's Littlest Pet Shop toy line.
This is the second episode that the ponies mistakenly call a rock slide an avalanche, the first being in "Dragonshy".
This episode is a reflection of the story of The Tortoise and the Hare, where the "slow and steady wins the race".
The scene where Rainbow Dash's wing is pinned under a rock is reminiscent of the film "127 Hours", where a man's arm is pinned under a rock. This scene features 1 pony, in season 2, episode 7. (1,2,7)