Holy crotch Ganon! 9 times Street Fighter IV Ö
I can't beat that but I've bought GTA: San Andreas 6 times. I love the game but I actually don't know why I bought it so many times. Well, part of it was because of it finally getting achievement and later on trophy support.
GTA: San Andreas - physical, PS2
GTA: San Andreas - digital, Steam (I got every single GTA game (excl. V) in a bundle for $10)
GTA: San Andreas - digital, Xbox 360
GTA: San Andreas - digital, PS3
GTA: San Andreas - digital, PS4
GTA: San Andreas - physical, PS3
Another game I've bought 6 times is Limbo.
Limbo - Xbox 360
Limbo - PS3
Limbo - Steam
Limbo - Vita
Limbo - Android
Limbo - PS4 (I think I got this for free with crossbuy though)
Other games I've bought more than 2 times are:
Time Commando
Wario Land II
Pokémon Silver (+ SoulSilver)
Diablo 2 (+ Gold)
Hitman (various)
C&C: Tiberian Sun
Fallout 3 (+ GOTY)
Borderlands 2 (+ GOTY)
Probably more due to Humble Bundles and Steam/GOG/Origin sales.
