Tottenham Hotspur Vs. AC Milan: UEFA Champions League Preview, First Leg

When I sat down to write a Tottenham Hotspur vs. AC Milan preview, I wasn't sure exactly how to approach it. We've never been to the UEFA Champions League knockout stages before, and we've had our fair share of slow starts/meltdowns this season. The game against Fulham was incredibly bad. Our match against Inter Milan at the San Siro was a disaster until Gareth Bale went all Welsh Jesus and made the scoreline look respectable. We all remember the first leg against Young Boys in Bern. We're good at collapses. I've got a really bad gut feeling.

To me, this feels like one of those typical Spurs collapse games *ducks*. What? Do you really have to throw things at me? Christ.

Luka Modric might be able to go on Tuesday, but it would be very surprising if he was able to go 90 minutes. Tom Huddlestone is still out, and he was a key piece in our good performances in Europe this season. As I'm sure you all know, we're going to be without Welsh Jesus. The lack of passing ability in the center of our midfield seriously scares the crap out of me. It's a really big problem.

Between the players we have injured and Milan's strengths and weaknesses, wide play is probably where we have the best chance to put together some serious attacking threats. Milan are likely to play with three, or maybe even four central midfielders who are either two-way players or defensive minded. They have shown a willingness to play both a narrow 4-4-2 diamond and a 4-3-3, with the former formation being more common. There's often space for opposing wingers to get the ball, and Milan's fullbacks are fairly questionable. Aaron Lennon could be Spurs' key player.

There are differing reports on whether or not Peter Crouch will be able to play on Tuesday, but from what I can tell, it looks like he's got a very good chance of making the squad. In most cases I would advocate that Roman Pavlyuchenko or Jermain Defoe gets the start over him, but on Tuesday, I'd rather see Crouch for a couple of reasons. First of all, Pav and Defoe's form. Neither of them were great against Sunderland and Defoe hasn't been good for quite some time. Second of all, the classic Crouch knockdown to Rafael van der Vaart is probably our best chance of scoring against a Milan team that is going to be very difficult to break down or counter attack on through the middle. Swinging in crosses to Crouch probably presents the biggest problem defensively for Milan.

On the other end, it's a tough call who they're going to play. Milan have four great forward options and they usually only start two of them, occasionally starting three. Zlatan Ibrahimovic is the only one of the four that is guaranteed a place, with the others rotating. If Max Allegri has done his homework, he'll be well aware that Tottenham's center of midfield poses little to no attacking threat. Additionally, Mark Van Bommel is cup tied, while Massimo Ambrosini, Kevin-Prince Boateng, and Andrea Pirlo are all injured. Therefore, he'll probably go with a three man midfield with three of his forwards up top. If I were a neutral or Milan fan, I'd want to see Ibrahimovic, Antonio Cassano, and Robinho as the front three in most games. Pato's been in mediocre form lately and I like how Ibrahimovic and Cassano can drop back into midfield and create just as well as they can score goals. Unfortunately for neutrals and Milanistas, Cassano is cup tied because of Sampdoria's unsuccessful UEFA Champions League qualifying campaign and Europa League play, so he will be unavailable in this tie. In general, though, he's made Milan quite a bit better. He might be a big miss on Tuesday.

So...what's going to happen. Like I said, I think we're in bad shape. I only hope that we can keep it respectable and score an away goal. Genoa and Lazio, who are both on the same level as us talent-wise when we don't have Bale and Huddlestone available, held Milan to draws in recent weeks. This is pretty encouraging. Obviously, I do think that we are capable of pulling off a scoring draw. I just wouldn't bet money on it.

Tottenham Hotspur projected lineup (4-4-1-1): Gomes / Assou-Ekotto, Gallas, Dawson, Corluka / Lennon, Sandro, Palacios, Kranjcar / van der Vaart / Crouch

AC Milan projected lineup (4-3-3): Abbiati / Yepes, Silva, Nesta, Antonini / Gattuso, Flamini, Merkel / Robinho, Ibrahimovic, Pato

Prediction: AC Milan 2-1 Tottenham Hotspur