Champions League Round of 16 • Tottenham Hotspur FC-AC Milan: The Big Money Question

Wednesday night. London. Can Milan advance to the Champions League Quarterfinals? That is when we will find out. With a 1-0 advantage from the first leg at San Siro, things were looking quite positive for Milan. Especially after Tottenham crashed and burned out of the FA Cup last week and then lost 1-0 to Wolves on Saturday as well. But then Fiorentina happened, and now Giroud reportedly has a fever. And, well, there is plenty of time for other important players to be injured or fall ill, too. Plus, we are playing away, which is so difficult for us this season for some reason. Sure, the Champions League is in Milan's DNA. But can Milan pull this one off? Can we out-mediocre the Spurs and answer the big money question?

Does this young side have what it takes to go through?

If there were one word that could sum up Tottenham's season, it would be inconsistent. After brilliant recent wins over Manchester City and Chelsea, they lost to Championship side (comparable to Serie B) Sheffield United and then 13th place Wolves in the space of four days. Since Conte's surgery, most of the matches have been managed by his longtime assistant, Cristian Stellini. Until this past week, he was a bit of a good luck charm, as Spurs had won all of the other matches he had been in charge of.

For the defeat to Wolves on Saturday, Stellini lined up: Forster; Romero, Lenglet, Davies; Porro, Skipp, Højbjerg, the formerly of Inter Perisić; the formerly of Juve Kulusevksi, Heung-Min Son; and Kane. Ahead of our first leg, I talked to Last Word on Spurs host Ricky Sacks about how Milan and Spurs have been eerily in some kind of Parallel Universe. Our serious injury plague seems to have transferred to them since that point. They are missing first keeper Llloris, as well as Bentancur, Bissouma, and Sessagnon to injury. Dier is also suspended for this one. Ouch. We know that pain. Meanwhile, Conte is planning to be back on the bench. Based on his history in Europe, that is great news for us. However, given these specific circumstances, he actually may motivate them to a win.

Conte has been recuperating with proper Italian food and should be ready to scream again.

Before the 1-0 loss to Fiorentina, I was invited to record a quick Milan preview for the Last Word on Spurs podcast in which I was quite positive. At that point, we finally had everyone back from longterm injury, with only Brahim Díaz a doubt for this one, and we were still in third place, tied on points with Inter. And Napoli had lost, too, so we could have made up a few points. Since then, we lost, now could be missing Giroud, and with Inter, Roma, and Lazio all winning this weekend, we have slipped to fifth in the league. Ouch. So much for being positive.

Pioli ended up still missing four players on Saturday, with Leão and Krunić suspended and Brahim Díaz injured, as well as Gabbia sick with a fever. Gabbia will probably be fine by Wednesday, but Giroud is a big worry, because Ibrahimović was not included on the Champions League list, and we need that big, physical presence up top in a match like this. Speaking of the list, Maignan has replaced Tatarusanu on our list, so we will have our first and third keepers, but not Tatarusanu.

Our attack could rely on Leão and De Ketelaere

Leão will have fresh legs and motivation, but has not actually scored for a bit. Brahim Díaz was the one who scored in the first leg, but he will most likely not be there. His replacement, De Ketelaere, seems to have an actual curse on him that prevents any ball he touches from breaking the plane of the opposition goal. So if we are also missing Giroud, that is literally our attacking three who are all unlikely to score. Not the way you want to go into a match that is worth at least €1 million just for winning, plus all of the millions for advancing to the quarterfinals, the television rights, etc. Well, there is Saelemaekers, aka Mr. Champions League, but that is only if Pioli starts him ahead of Messias, who has started in the last three matches in that spot.

Looking at form, it is like two people at a doorway, both insisting "After you." "No, after you, I insist." Neither team seems to want to win this season. Whichever team goes through will either be incredibly lucky or perhaps just win unintentionally. Conte could threaten his players into playing up to the level of their salaries and transfer fees, in which case, Milan has no chance in comparison. Or, Milan could do the impossible again, like last year, when they won the Scudetto. But will they be able to? That is the big money question.

This post inspired by the music of The Beatles' "Can't Buy Me Love"

Our next match is 
Champions League Round of 16
Tottenham Hotspur FC vs. AC Milan
Wednesday, March 8, 2023 • 21:00 CET (3pm EST)
This match can be streamed LIVE on Paramount+ in the U.S.

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Champions League Round of 16 • Tottenham Hotspur FC-AC Milan: The Big Money Question Champions League Round of 16 • Tottenham Hotspur FC-AC Milan: The Big Money Question Reviewed by Elaine on 11:00 PM Rating: 5
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