Round 1, Match 5
Beauty v Pegasus
Like the previous match, these two don't have much in common. They both start literary, but they've also both had their share of film appearances. Other than that, they're pretty much black and white. Literally.
Beauty is the eponymous star of possibly the best horse book of all time (I'll fight you over that), Black Beauty. His story shows the horrible fates waiting for horses in Victorian England, though his is eventually a happy ending.
Pegasus is the equine star of the best mythology of all time. (I'll fight you over that one, too.) He's captured by the greek hero Bellerophon, who rides him to defeat the three-headed Chimera. (Also, if you want to laugh really hard, his Wikipedia article has an actual pedigree chart for him and it's amazing.)
Who'll it be? These are two of the most well-known archetypes in the equine fiction world, so choose wisely.
The cover of my favorite copy of Black Beauty
Pegasus. There are a LOT of slightly weird images of pegasii on Google Images.