Milan returned to winning ways with a narrow victory over Torino on Friday, while the visitors need to pick themselves up after being thrashed 4-1 by Leicester City at the weekend.
Match preview
After enduring a torrid seven-game winless run - which included defeats to their great rivals Inter in both the Italian Super Cup and the league - AC Milan knew only a win would do against Torino in Friday's Serie A offering.
The Rossoneri had only been knocked out of the Coppa Italia by Ivan Juric's side last month, but they exacted revenge for that extra-time defeat, with Olivier Giroud heading home just after the hour mark to guide Milan to just their second win of 2023.
An unconvincing but precious victory helps alleviate some of the pressure that had been building on Stefano Pioli, but with his side 18 points adrift of league leaders Napoli and out of the domestic cup, the Milan boss needs a positive performance form his side in the Champions League.
Although Milan are seven-time European champions, Tuesday's meeting with Tottenham will represent the club's first Champions League knockout round tie since they were beaten 5-1 on aggregate by Atletico Madrid in the last-16 in the 2013-2014 season.
The reigning Italian champions have been eliminated at the last-16 stage in five of their previous six appearances in the competition - including in the 2011-12 campaign when they lost 1-0 on aggregate to Tottenham - and having failed to win any of their four competitive meetings with Spurs, Milan know that they will have their work cut out to progress to the quarter-finals.
After recovering from gallbladder surgery, Antonio Conte's return to the touchline looked set to coincide with a positive result when Rodrigo Bentancur gave Tottenham the lead in Saturday's away encounter against Leicester, but it turned out to be a forgettable afternoon for the North London club.
Nampalys Mendy, James Maddison, Kelechi Iheanacho and Harvey Barnes all got on the scoresheet to condemn Spurs to a heavy 4-1 defeat, which makes their 1-0 victory over Premier League champions Manchester City feel like a distant memory.
Tottenham will now have to pick themselves up and dust themselves down as they dream of replicating their memorable run to the Champions League final, which took place under Mauricio Pochettino's guidance in the 2018-19 campaign.
In contrast, they will not be keen to relive memories created from their most recent last-16 appearance, where they were thumped 4-0 on aggregate by RB Leipzig, which included a miserable 3-0 defeat in the away leg, but that took place under Jose Mourinho's watch rather Conte, who may be relishing a meeting with an old foe.
Conte's recent record against Tuesday's opponents makes for positive reading if you are of a Tottenham persuasion, with eight of his last nine games against Milan yielding a victory, including a 3-0 win in his most recent away game against the Rossoneri in 2021 when he was manager of their city rivals Inter Milan.
AC Milan Champions League form:
D
W
L
L
W
W
AC Milan form (all competitions):
D
L
L
L
L
W
Tottenham Hotspur Champions League form:
W
L
D
W
D
W
Tottenham Hotspur form (all competitions):
L
L
W
W
W
L
Team News
First-choice goalkeeper Mike Maignan has not played since September due to a calf injury, and while Milan are hopeful the Frenchman will return for the second leg, he has been ruled out of Tuesday's contest, ensuring Ciprian Tatarusanu will continue to deputise in his absence.
Following a spell on the sidelines, Ismael Bennacer and Fikayo Tomori could both recover in time to feature in the starting lineup.
The unmistakable figure of Zlatan Ibrahimovic returned to the Milan bench on Friday - the first time since May 2022 - but after spending an extended period on the sidelines, he had to settle for being an unused substitute, and he is unlikely to get any minutes against Tottenham.
Like their hosts, Tottenham are also unable to call upon their first-choice shot-stopper, with Hugo Lloris ruled out with a knee injury, ensuring Fraser Forster will feature for a second straight game.
Cristian Romero was suspended for the Premier League meeting with Leicester, and he will replace Japhet Tanganga in the lineup on Tuesday, joining Eric Dier and Ben Davies in a back three.
Bentancur sustained a season ending anterior cruciate ligament injury on Saturday, and with Yves Bissouma injured and Pierre-Emile Hojbjerg suspended, Tottenham may be forced into fielding the untried midfielder pairing of Pape Matar Sarr and Oliver Skipp.
AC Milan possible starting lineup:
Tatarusanu; Kalulu, Kjaer, Tomori; Saelemaekers, Bennacer, Tonali, Hernandez; Diaz, Leao; Giroud
Tottenham Hotspur possible starting lineup:
Forster; Romero, Dier, Davies; Emerson, Sarr, Skipp, Perisic; Kulusevski, Son; Kane
We say: AC Milan 1-1 Tottenham Hotspur
Spurs will head to Italy in a downbeat mood following Saturday's poor performance and the news that Bentancur will miss the rest of the season through injury.