Both clubs are in a state of flux - only one player from Arsenal's starting XI in that 2008 match-up, Bacary Sagna, will be in Arsene Wenger's lineup this time.
Milan are going through their own period of change and, like Arsenal, it has not always been to the liking of their crowd. A perception has grown that they have sacrificed some of the old panache to play in a more functional manner — epitomised, perhaps, by the presence of the Dutch enforcer Mark van Bommel in midfield.
The contrast of the two teams can be identified by their high expectations based on their proud past success - Arsenal is looking to develop that edge or grit that marked their teams that were led by Patrick Vieira, Tony Adams, and Emmanuel Pettit. Dennis Bergkamp believes the current Arsenal team are too predictable and need to develop "more of a winning mentality than a passing mentality".
AC Milan are going through a period where they are trying to find their identity, and resembles a more workmanlike team than the more creative and attacking-oriented teams of their past UEFA Champions League successes. This team plays with more perspiration, less inspiration.
Or as Milan coach, Massimiliano Allegri put it: "You can't always dine on lobster and caviar. Every now and again you have to be satisfied with a ham sandwich."