Most times you've bought a single game?

[Plerpy_]

Final Fantasy X and X-2 I think.

2002 - PS2 version originals (my brother kept these)
2010 - PS2 used copies (to replace the above)
2010 - PS2 brand new shrink wrapped copies (because I wanted them new for some reason)
2014 - PS3 remasters
2016 - PS4 remasters