FFT, paid for 5 times.
Two for the PSX version (scratched CD) and once more for the PSN version
Once for a physical copy of WotL then once for a digital copy once I lost the UMD

FF7, FF9, Xenogears, Chrono Cross
Original Game + PSN

Mega Man X: Maverick Hunter (PSP) Twice
Once on UMD and then another digital copy after I lost it with my copy of FFT:WotL