This week marks the return of Champions’ League football to the European calendar, with the first night featuring Tottenham going back to the San Siro, this time to take on A.C. Milan.

Last time they were in Milan, Spurs started out about as badly as is possible, being 4-0 down at half time and down to 10 men against Internazionale (a position they enjoyed so much, they repeated it against Fulham in the FA Cup last month).  A second half hat-trick from Gareth Bale gave Tottenham some confidence, which led to them beating the reigning European Champions at home and they ended up qualifying for the last 16 top of their group.  Inter, though, have been on a downward trend this season and Spurs must now take on an A.C. Milan team who have been leading Serie A since the beginning of the campaign.

A.C. Milan have a host of attacking talent which will really test out the quality of our defence.  The trouble is, all season that defence has looked like it will collapse quicker than a Middle Eastern government once protesters hit their capital’s main square.  Three times in cup competitions this season, Spurs have been three goals behind within the first half an hour of play (the aforementioned Inter and Fulham games, plus the away leg of the Champions’ League qualifying tie with Young Boys of Berne). With Robinho, Pato and Ibrahimovic likely to start for the Rossoneri, we are going to need concentration for all 90 minutes from our starting centre backs, Dawson and…Sorry hang on a moment, just need to change my shoes…hope I didn’t miss anything important…right where was I? Oh yeah, William Gallas.

(On that incident, where Gallas was changing his boots while Sunderland scored on Saturday, there’s a half-hour period before the game where players can get used to the turf and warm up their muscles, why didn’t Gallas know which studs he should be wearing before the game, rather than 10 minutes into it? Or was it the shade of yellow that he was intent on changing?)

Spurs will be missing possibly both of their main talismans (worst.plural.ever) of this season – with Gareth Bale definitely out and Rafael Van der Vaart struggling with a calf strain – as well as the mercurial Luka Modric – who is missing both this game and, as of two weeks ago, his appendix.  These absences have definitely had an effect on recent performances, though hard fought wins over Sunderland, Bolton and Blackburn have kept us in the hunt for qualifying for next season’s Champions’ League, it raises major questions as we reach the knockout stages of this year’s competition.  If Tottenham were going in with Bale, Van der Vaart and Modric, as well as other absentees Huddlestone, King and Woodgate, I would be very confident in their ability to match up with most other sides.  Without them? It’s a tough call.

I expect Spurs to come out and attack Milan, who will respond in kind.  Milan’s once fabled defence is no longer as rock-solid as those teams of the mid-90s, but they have still only conceded 19 goals in their 25 league matches this season.  Sitting in front of the back four, Gattuso is nowhere near the player he was in 2006 during Italy’s World Cup triumph, and, should we have Van der Vaart available, I’d expect him to be able to enjoy time and space in that part of the pitch.  There are areas of opportunity to Tottenham should they come out and play well, but Milan will punish anything less than our best performance.

Given the second leg is not until March 9th, when Tottenham will be back to some semblance of full strength, I hope Spurs can at least stay within a goal of Milan and give them a good game at the Lane.  My prediction: Milan 1-1 Tottenham; Tottenham 3-1 Milan. Well, I can dream…

Other ties:

Valencia vs. Schalke – Valencia to go through

Arsenal vs. Barcelona – Bias maybe, or just because they’re the best team in the world, Barcelona to go through in a romp (or two)

AS Roma vs. Shaktar Donetsk – Shaktar to squeak through

FC Copenhagen vs. Chelsea – The Blues have only been the 10th best team in England since the start of November, but they’ll still have enough quality to get through this round. No further though, unless they have an equally kind draw (and I don’t mean Tottenham!)

Lyon vs. Real Madrid – Madrid are probably the best second placed team in history, Lyon are not the force in this competition they were a few years ago. Real to progress.

Inter Milan vs. Bayern Munchen/Bavaria Munich (pick one, but Bayern Munich makes no sense, as my sister loves to tell everyone. Also, that Schweinsteiger means “pig-climber”. Fact) – A repeat of last season’s final, but these two heavyweights have been more like pub brawlers this season.  I’m going to say Inter will get through because Leonardo has come in and made them play more like a team, plus they have the fantastic Eto’o to get them goals.

Marseille vs Man United. – not sure if you’ve heard, but Rooney scored something of a cracker on Saturday – that could just be the catalyst to get him back in form.  Either way, can’t see United coming unstuck here, though Marseille have only lost one of their last 12.