My Big winners:

Cloud vs. Zidane: Cloud
Vincent vs. Amarant: Vincent
Cid vs. Freya: Freya
Aeris vs. Garnet: Garnet
Yuffie vs. Eiko: Yuffie
Barret vs. Steiner: Tough one, I'd go fo Seifer if Vivi was with him, if not Barret would win
Tifa vs. Vivi: hmmm also a tough one, I think Tifa
Red XIII vs. Quina: Quina if he/she learnd a lot of good stuff