Low-scoring first leg at San Siro?
Already in the 2010/11 season, AC Milan and Tottenham faced each other in the last 16 of the Champions League. Spurs won the first leg 1-0 at the Giuseppe Meazza Stadium thanks to a Peter Crouch goal, before the Londoners held them to a goalless draw in the second leg. Even now, on balance, the betting on the Lilywhites progressing in AC Milan v Tottenham is under the more favourable conditions.
In 2023, the Rossoneri were finally deep in crisis. AC Milan remained winless in seven consecutive competitive matches (two draws, five defeats), but managed to break the negative run in Friday’s dress rehearsal (1-0 against Torino FC) of all things. Spurs, on the other hand, suffered a 4-1 defeat at Leicester City in their dress rehearsal, which should be taken into account in AC Milan’s forecast against Tottenham.
When the current fifth-placed team in Serie A clashes with the fifth-placed team in the Premier League, it is also two teams that are not exactly brimming with confidence. There is a lot to be said for a long period of rest and a tactical game in which neither team wants to make the decisive mistake. Similar to the round of 16 in the 2010/11 season, when a single goal in the first and second legs decided who would advance, it could be a low-scoring affair.
We therefore see the greatest value in betting on a maximum of two goals in the first leg at the San Siro, whereby we consider a home win for the Rossoneri, who have not won against English teams for ten competitive games (two draws, eight defeats), to be the least likely.
AC Milan – Statistics & current form
AC Milan have won the Champions League or European Cup of Champions seven times and remain the team with the most overall victories behind Real Madrid in the all-time list.
Last summer, the Rossoneri also won the Scudetto for the first time in eleven years, before a second-place finish in Group E behind Chelsea and ahead of Salzburg and Zagreb put the Lombard team into the last 16 of the top flight for the first time since 2013/14. Nine years ago, they suffered an emphatic 5-1 defeat to Atlético Madrid here after first and second legs.
Without scoring in nine of last 14 Champions League knockout matches
In general, the record of “Il Diavolo” in the knockout rounds of the Champions League reads anything but good. Milan have won just two of their last 14 knockout matches in the top flight (three draws, nine defeats) and have failed to score in nine of those 14 games.
The Italians, who have never won against Tottenham before (two draws, two defeats) and have not won against a Premier League side in ten competitive matches (two draws, eight defeats), will have a tough time of it.
Won only one of their last eight competitive matches
After all, the Rossoneri did manage a 1-0 home win against Torino FC on Friday, putting a stop to their freefall in Serie A thanks to Olivier Giroud, who has already contributed to six goals in the top flight (four goals, two assists). In fact, however, it is the only victory for “Il Diavolo” from the last eight competitive games (two draws, five defeats).
It is therefore all the more surprising that the betting odds on AC Milan against Tottenham are slightly in favour of the Lombards, who won their last Champions League home game against Salzburg by a clear 4-0 margin but have not celebrated two consecutive home victories in the top flight since September 2013.
Last matches of AC Milan:
Serie A
11/02/2023 – AC Milan 1 – 0 FC Torino
06/02/2023 – Inter Milan 1 – 0 AC Milan
29/01/2023 – AC Milan 2 – 5 Sassuolo
25/01/2023 – Lazio Roma 4 – 0 AC Milan
Super Cup
19/01/2023 – AC Milan 0 – 3 Inter Milan
Tottenham – Statistics & current form
Tottenham Hotspur have won two other UEFA competitions, the European Cup Winners’ Cup (1963) and the UEFA Cup (1972 and 1984). However, the Londoners have yet to win the Champions League. In the spring of 2019, they suffered a 2-0 defeat in the final against Liverpool in Madrid.
Since then, the Lilywhites have only reached the last 16 once before in the 2019/20 season, where they were beaten 4-0 by RB Leipzig in a first and second leg. With eleven points out of a possible 18, they won their group ahead of Frankfurt, Sporting Lisbon and Olympique Marseille in the current season.
Lost five of last six knockout games in Champions League
The Londoners’ recent international record doesn’t read too impressively, though. Tottenham have lost five of their last six knockout matches in the top flight (one win) and have failed to score in each of the last three of those games.
At least in this year’s group stage, however, there have been four games in a row without defeat (two wins, two draws). It is therefore by no means out of the question that the bet on AC Milan against Tottenham will go in favour of Spurs.
Lost three of last six competitive games
The dress rehearsal, however, went badly wrong for the North Londoners. After a remarkable 1-0 home win over Manchester City the weekend before last, Spurs went down 4-1 away to Leicester City on Saturday. Overall, it was the third defeat in the last six matches (three wins).
Antonio Conte, who has won eight of his last nine competitive games against AC Milan (one defeat) but will not be able to travel to Italy because of a gall bladder infection, has done well against Serie A opposition. Tottenham have always scored at least one goal of their own in nine of their last ten competitive matches against Serie A sides.
Last matches played by Tottenham:
Premier League
11/02/2023 – Leicester 4 – 1 Tottenham
05/02/2023 – Tottenham 1 – 0 Manchester City
FA Cup
29/01/2023 – Preston 0 – 3 Tottenham
Premier League
24/01/2023 – Fulham 0 – 1 Tottenham
20/01/2023 – Manchester City 4 – 2 Tottenham
AC Milan – Tottenham Direct comparison / H2H balance
Head to head: 0 – 2 – 2
The two sides have faced each other four times in competitive matches so far and Milan are yet to record a first win against Spurs, having beaten the Rossoneri in both the 1971/72 UEFA Cup semi-final and the 2010/11 Champions League last 16. Most recently, the Londoners managed a 1-0 away win at San Siro in the first leg of the top flight, which was overturned in the second leg (0-0).
AC Milan – Tottenham tip
When predicting AC Milan against Tottenham, it must be taken into account that both teams have been struggling recently. It is not for nothing that both opponents are currently “only” in fifth place at national level and would have missed out on qualifying for the top flight again as things stand. It should be taken into account that in the knockout stages of this competition, too, there have been more failures than successes on both sides in recent times.
Two teams that do not go into this first leg with the greatest momentum are likely to be primarily concerned with not falling behind and not taking any unnecessary risks. A lot of value is therefore provided by betting on a maximum of two goals.
