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Antonio Conte has won eight of his last nine against Milan
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Olivier Giroud in fine form in the Champions League
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2.29 Bet Builder looking a good option
Milan v Tottenham
Tuesday 14 February, 20:00
Live on BT Sport 1
Milan come crashing back down to earth after remarkable season
Milan are currently just fifth in Serie A, although admittedly on the same number of points as Roma and Atalanta in fourth and third place, respectively.
Still, it's a far cry from that fabulous Serie A title last season.
But at least they negotiated their way into the Last 16 of the Champions League without much hassle, finishing runners-up to Chelsea. They secured back-to-back 4-0 wins, first at Dinamo Zagreb and then at home to Salzburg, those six points and a strong goal difference meaning they were never in much danger of not qualifying.
Worryingly though, before that, they had lost 3-0 at Stamford Bridge and then 2-0 at home in the reverse fixture. And let's face it: the Blues are hardly having a great season themselves.
Remarkably for a side that has historically been such a big player in this competition, Opta remind us that it's their first appearance in the knockout stages of the Champions League since the 2013-14 season.
If his form in the Champions League so far is anything to go by, then much will depend on veteran Olivier Giroud. He's been involved in six goals so far this season, scoring four and assisting two, and may have a point to prove here. He had a three-year spell at Chelsea (before moving to Milan) that started well but fizzled out somewhat.
Other players to look out for are Portuguese winger Rafael Leao and Theo Hernandez, who love to combine down that left wing. Keeper Mike Maignan is likely to miss out with a long-term injury, with Milan hoping he'll be available for the second leg.
Inconsistency plaguing Spurs
Spurs' results in the Premier League over the last two weeks tell you everything you need to know about their inconsistency this season.
The weekend before last they put in an extremely professional and organised performance to beat Manchester City 1-0 at home but followed it up with a horror show this weekend just gone. Despite taking an early lead, they then conceded four to lose 4-1 at Leicester.
Interestingly, they're in the same fifth place in their domestic league as Milan are.
But unlike Milan, they topped their Champions League group. Key to that was their good home form, beating runners-up Frankfurt and Marseille and drawing with Sporting Lisbon.
Another curious similarity between the two is that Spurs are also missing their first-choice goalkeeper with Hugo Lloris ruled out for another six weeks or so.
But they suffered an additional blow with the news that Rodrigo Bentancur is out for the season after injuring his knee in that defeat at Leicester.
Draw the lesser of three evils
The odds are pretty tight here with home advantage the main reason why Milan are slight favourites at 2.6813/8, with Tottenham available at 2.915/8 and the draw a 3.4549/20 chance.
Simplistic as this sounds, in a game where there doesn't seem too be too much to choose between them, going for the biggest price of the three (the draw) at 3.4549/20 makes some sense.
What could make a big difference here is Antonio Conte's remarkable record as manager against the Rossoneri. Opta point out that he won eight of his nine matches against them between 2013 and 2021. Better still, he's guided his team to three consecutive wins at the San Siro without conceding a single goal in any of them.
Goalscorer watch
On the goalscorer front, you could make a case for Milan's top two scorers this season.
Giroud has been good in this competition so far as we've seen already, is fresh from scoring in their 1-0 win over Torino on Friday night, and also got one two weeks ago in a shock 2-5 defeat at home to Sassuolo. So the Frenchman comes into this match in decent form.
Spurs keeper Lloris hasn't had the best of seasons by his high standards but experience goes a long way and Milan's chances of scoring increase as a result of his absence. Giroud is 21/10 on the Sportsbook to get a goal but as we always say, check out his price on the Exchange nearer the time, as well.
Leao, with nine goals of his own, is decently-priced at 3/1 on the Sportsbook but you may well get 5.04/1 or better on the Exchange.
Harry Kane is the obvious place to start as regards Spurs players with 17 in 23 Premier League games but he hasn't been quite as consistent in this competition with just the one goal so far. He's their best chance of a goal, of course, but for that reason, the 7/5 looks a little short.
Bet Builder the bet of the match
This is an extremely tough match to predict with lots of ifs, buts, and maybes.
So maybe the best bet lies in the form of a Bet Builder.
Conte's remarkable record against Milan and Spurs' far greater recent experience in the knockout stages of this competition suggest Spurs won't lose here so the 4/9 on the Double Chance market (Spurs win or draw) is a good starting point.
The stats don't necessarily suggest this could be a 'both teams to score' game so we're going a bit against the grain in that sense here. But these are two well-matched sides, missing their first-choice keepers, and are both capable of putting in poor performances at the back. So it would be a bit of a surprise if we didn't see both sides score at least once.
The double comes to 2.29.