|Family:|| Alfred Sinclair (Ancestor)|
Victor Sinclair (Grandfather)
|Voice Actor||James Shubert|
|Anime Debut||Bleeding is embarrasing|
Winner Sinclair (ウィナー・シンクレア) is a descendant of Alfred Sinclair. He only appears in the anime.
He was raised as a vampire slayer. He wasn't born in Japan but visited there once before. He was the first victim of Karin.
When he first appears in the anime, he is totally infatuated with Karin , calling her his "Ideal Woman", and even challenging Kenta Usui to a duel every day for Karin's affection. While dueling, Karin interupts, but immediatly has another nosebleed. At the sight of blood, Winner passes out (indicating him to possibly hemophobic). Later, while patroling for vampires, Winner's cross necklace breaks without him noticing. A passing Henry Marker notices and returns it to him. He thanks him, not realizing that one of the vampires he was searching for just handed him his cross. Winner is amazed that even in the city there are still kind people. Actually, Winner first appears in the very beginning of the first episode. During that time, he is the one who was bitten by Karin at the dock. His first kiss was with Karin, but in truth it was her first bite and because of the memory loss, he though it was a kiss. Karin's best friend Maki falls in love with him and confesses to then be rejected because he still feels he is in love with Karin.
- The most prominent trait Winner has is the inability to take a hint.
- He pursues Karin, despite the obviousness of her not wanting to have anything to do with him.
- Both Maki and Kenta try helping him see this, but Winner persists.
- He jumps to conclusions.
- He has fear to the blood as Naga from Slayers and Tsunade from Naruto
- He seems to have a habit of calling his classmates from school by their relationship to Karin (e.g. calling Maki "Miss Karin's friend and sidekick"). However he breaks this trend at least once, calling Maki "Miss Maki" after she confesses to him and kisses him.