Most WTF Nickname: Teenage Pimples (Drybones446)
Most Random Nickname: Aiming for Anorexia (Sinnohdragon)
Most Creative Nickname: Sylux (Dark Petal)
Best Nickname: Circuit Breaker (PokemonHero)
Most WTF Nickname: Machop's Blue Jump Rope (pikasaur)
Most Random Nickname: Squidward (OrangeDonphan)
Most Creative Nickname: Martini (shiny_arceus)
Best Nickname: Tsubasa (Sushi Bunny)
Most WTF Nickname: Go die in someone's mouthmin (Dragodynamite)
Most Random Nickname: Evidential Wooden Pavement of Generic Fascism (Rheine)
Most Creative Nickname: Verde (magic_eevee)
Best Nickname: Eden Embodied (darkdragontamer)
Aiming for Anorexia just made me lol so hard.
With the Japanese release of HG/SS, I think it's fair that the Nicknaming Contest gives special tribute to it through this set, don't you think?
Chikorita: Chik-or-Rita, Tea Leaves Covered in Ash, Green Hack Throwback
Cyndaquil: Black White and Red All Over, Baby Bowser, Lizards On Fire
Totodile: Dile T for turtle, Hyper Blue Sugar Stuffer, Can-Opener
Is it possible for one person to win on 2 pokemon in 1 round, DM?
While not entirely impossible, I would say it's extremely unlikely. I try to ensure (maybe that's not the word for it) that there are twelve completely different winners for each set. There has only been one case (which was in the past Nicknaming Contest) where someone has won in more than one title in a single set.