UCL Magazine - Di Maria, Zubimendi and Buruk interviewsSep 29
Spurs were humiliated at Leicester on Saturday and will be looking for a response against the Italian champions at San Siro.
Milan, meanwhile, are on a dismal run of form since the turn of the year, winning just two of nine games in all competitions and falling to fifth in Serie A.
That doesn’t bode well for the Italians, but can Spurs take advantage? Here are three reasons to look forward to one of the standout ties of the last 16, live on BT Sport 1.
Conte back in Milan
Milan supporters will know all about Antonio Conte.
The Spurs boss was in charge of rivals Inter before his move to north London and won the Serie A title in the 2020-21 season, with Milan finishing second.
There is history there then and that will only add to the spectacle as Conte looks to get another one over an old foe.
He was back in the dugout at Leicester and will travel with the team after undergoing surgery to remove his gallbladder at the start of the month.
Much has been made of his record in the Champions League - he has only reached the quarter-finals once, with Juventus in 2013 - and he will want to set that straight.
Porro preparing for action
Tottenham’s most notable January addition endured a debut to forget against Leicester as Spurs fell to a 4-1 defeat at the King Power.
It was a miserable start for the former Sporting Lisbon right-back who could be given an opportunity to kick-start his Spurs career in Milan.
Emerson Royal impressed in the recent league win over Man City but Pedro Porro, signed initially on loan from Sporting, should offer more in an attacking sense.
And there will be plenty of excitement if the Spaniard is named in the team that travels to Milan. The suggestion is that with more offensively competent wing-backs in place Conte’s style of play will become more effective.
Porro will be the man to watch at Spurs over the next few weeks as they look to reach the latter stages of the Champions League.
Giroud faces old rivals
It’s not just Conte who will be taking on a former adversary on Tuesday night.
Olivier Giroud was at Arsenal for six years and played in many north London derbies during his time at the club.
The Frenchman played for Chelsea after leaving the Gunners, too, so his popularity amongst Spurs fans is unlikely to be high.
Giroud will be keen to put on a performance in one of the biggest games of the season, particularly given his struggles for form since the World Cup. After his brilliant displays for France in Qatar the 36-year-old has scored just twice in 2023 for Milan.
But he is often the man for the big occasion and Tottenham will be wary of allowing him to become the focal point for Milan in attack.
With Harry Kane in fine form for Spurs at the other end of the pitch, this tie could well swing on the performances of the two strikers.