What's the most number of times you've beaten a game?

[Kyuu]

RE5 at about 10 times (co-op with a number of friends).

Besides this and maybe Touhou 8, I didn't finish any game more than 3-4 times (Shadow of the Colossus, Bloodborne, RE1 Remake, RE4, FF6, FF8, FFX, maybe DMC1, 3 and 4). Not counting fighting games arcade mode.

These days I rarely finish a game more than once.