No, he does not win the Springfield Cup, but instead it was a draw. However, he did excellently to get a draw, considering he is only 10 years old and his final round opponent is The Thousand Blade, Jack Rakan of Ala Rubra.
Judging by the books I would say he loves asuna the most, but nodokas pretty high up there.[Edit]Asuna, based on all of what happens, is probably his favorite; but them getting married, having kids,...
Negi starts out as 10 in the beginning, but as of chapter 300ish and on, he is probably supposed to be 12 or something. In chapter, oh, 351--352-ish, he's apparently "dead" but I don't believe it...
Truth be told it STILL hasn't been told. (So I believe) It shows (SPOILER) Kotaro marrying the obvious, as well as many others, but it doesn't truly explain who Negi goes with. As read, it isn't...
Dusty Springfield never won a Grammy, however her album DUSTY IN MEMPHIS (Atlantic Records 1969) is enshrined in the Grammy Hall Of Fame as one of the best ever albums.