Last year, I was one of Harry Redknapp's biggest critics for his marriage to the 4-4-2 formation. No matter who the opponent was, what personnel was healthy, and what kind of result we were realistically shooting for, it was all 4-4-2, all the time. I'm not the only one who criticized Harry heavily for this, and we've all been very happy with our transition to a 4-4-1-1 setup where Rafael van der Vaart plays behind a central striker. However, there is a time and place for everything. Tottenham Hotspur's UEFA Champions League second leg matchup against AC Milan is one of those times and places for 4-4-2.
As Ryan Rosenblatt pointed out on SBNation.com, the Rossoneri have no options in the center of midfield. Mathieu Flamini will start, but after that, it's a crap shoot. Clarence Seedorf will likely start out of necessity, but he doesn't give the team much in the way of defensive qualities. Alexander Merkel is a decent young player, but he's 19 years old and very unpolished. Kevin-Prince Boateng is likely to make the bench, but he's also unlikely to play unless there's an emergency (like Flamini or Merkel goes down and Milan still have a chance to win). It's possible that Thiago Silva could step back up into a defensive midfield role, but he's not a natural in that position and he had a poor game in the first leg.
My projected lineups for Tottenham Hotspur vs. AC Milan can be found here. You'll see that I predicted a Jermaine Jenas-Luka Modric center of midfield. Sounds scary, right? Usually, I would say that Harry was out of his mind and that Spurs were going to get overrun. But come on, look at what Milan has available in midfield!
Spurs out-played Milan in the first leg, and that was when they had Gennaro Gattuso. Rino is now suspended, and Merkel is likely to step in his place. It seems highly unlikely that the players who will be involved in the game for Milan will be able to win the midfield battle, so there's really no need to play three in the center just for the sake of playing three.
I'm not a big "compromise" guy. I think you go big or go home. So, I don't even see 4-4-1-1/4-2-3-1 as an option. I think that Spurs should either go with a 4-4-2 with two wingers and play old school Harry ball or pack the midfield with a 4-4-2 narrow diamond, completely dominate that area of the pitch, and just hold onto the ball for long periods of time. Milan don't have any wingers, so the only negative to doing this is the fact that Aaron Lennon would be left on the bench. Milan need to score twice for us to be in trouble, so I'm totally okay with this.
I don't really like old school 4-4-2, but there is a time and place for everything. The time and the place for Harry Ball is today.