Loathe as I am to say so, Cloud wins this match. While he never did make SOLDIER, Cloud does have military training, and his higher-end attacks and ability to make use of Materia give him the definitive edge on Umaro. Umaro is brutish and not terribly bright, so while he has immense strength Cloud's ability to think tactically and make use of long-range magic and summons gives him the win.

Cloud still sucks though.