I voted for the game 7 winner in 09.
That will probably win, but I like to forget anything that happened in those playoffs.
Cleary was awful in the 2008 playoffs, but the Wings won the Cup. In 2009, he was brilliant and scored a lot, but the Wings lost and he missed that crucial breakaway at the end of game 6 against the Pens.
2007 is a better memory, because the team vindicated itself after choking in the playoffs in 2003, 2004 and 2006. Losing to Anaheim on a deflection sucked, and I still feel we'd have won the Cup if not for that play, but overall, that playoff feels better. Also likely because we won the Cup the following year. 2009 still stings because the Wings haven't won anything since then.