Twice, I think. And once with New Game+.
I tend not to play through the entirety of a game several times; usually I'll start a new playthrough and move to another game instead half-way. I have a serious crapload of uncompleted CT and FFIX save files, spread across different sections of the game. It's the case with a lot of my RPGs, actually...
As for Cross, finished it once, New Game+ wasn't possible on an emulator, and my PC died shortly after the start of my second game. Currently playing a new game on my PSP.