The two former continental champions will play their first Champions League games under new management this week, and both Arne Slot and Paulo Fonseca have some recent wrongdoings to rectify.
Match preview
Before passing the Anfield torch over to Slot, Jurgen Klopp succeeded in his quest to bring Champions League football back to the Liverpool faithful, albeit with a third-placed Premier League finish rather than the Europa League crown that many foresaw at the start of the season.
Between now and the end of January, the six-time European champions will engage in a handful of blockbuster ties in the new-look league phase; Anfield showdowns against reigning champions Real Madrid and Xabi Alonso's Bayer Leverkusen are particular highlights.
Bologna, RB Leipzig, Girona, Lille and PSV Eindhoven will also endeavour to prevent Liverpool sailing through to the last 16 as one of the top eight teams in the 36-club league phase, where the sides ranked ninth to 24th will have a playoff safety net, while outfits finishing 25th to 36th will crash out of Europe altogether.
The Reds make the trek to San Siro with four wins under their belt from their last five away games versus Italian clubs in European competition, but they were memorably sent packing by Atalanta BC in last year's Europa League quarters and were a shadow of their usual selves at the weekend.
After winning each of their first three Premier League games of the season without conceding a single goal, Liverpool slumped to a humbling 1-0 loss to Nottingham Forest courtesy of an exquisite Callum Hudson-Odoi strike, as the former Chelsea wonderkid punished Liverpool's alarming profligacy in front of goal.
While this week's visitors to San Siro suffered their first defeat of 2024-25 at the weekend, AC Milan coincidentally got up and running at the fourth attempt, having failed to take maximum points in any of their first three Serie A showdowns under Paulo Fonseca.
The former Lille and Roma manager only took two points from his first three games in charge of the Rossoneri, leading to extremely premature talk of the sack, but the international break clearly did both him and his troops the world of good if Saturday's display against Venezia was anything to go by.
Within just 29 minutes of that league contest, Milan had already struck a quartet of goals through Theo Hernandez, Youssouf Fofana, Christian Pulisic and Rafael Leao, and Fonseca's men ultimately declared at 4-0 as the 51-year-old belatedly registered victory number one.
The Rossoneri boss now has an extremely tough act to follow in the Champions League, being just the second Portuguese man to take charge of an Italian club in the competition after Jose Mourinho, who masterminded Inter Milan's run to the 2009-10 title.
Tuesday's hosts will also pit their wits against Real Madrid, Leverkusen and Girona in league phase action, as well as Club Brugge, Dinamo Zagreb, Slovan Bratislava and Red Star Belgrade, but the Rossoneri fans will hope that revenge is the first dish on the menu in midweek.
The 2005 miracle of Istanbul was already avenged in the 2006-07 Champions League final, but Liverpool emerged victorious in both group-stage matches during the 2021-22 season, where cult hero and now-Milan outcast Divock Origi was one of the scorers in a 2-1 win at San Siro.
AC Milan form (all competitions):
Liverpool form (all competitions):
Team News
Despite having a handful of training sessions under his belt before the visit of Forest, Liverpool new boy Federico Chiesa did not make the squad for the Reds' latest Premier League game, as Slot is being especially careful with his fitness.
A debut for the Italian attacker in his homeland has not been ruled out, but the tight turnaround means that he is still a serious doubt for the trip to Milan, where Harvey Elliott is definitely out due to his foot fracture.
Neither Cody Gakpo nor Darwin Nunez had the desired impact up front after coming off the bench on Saturday, but with a little over 72 hours in between matches, Slot will certainly consider freshening up his starting XI with the introductions of the attacking duo.
As for Fonseca's Milan, all of Ismael Bennacer (ankle), Alessandro Florenzi (ACL) and Marco Sportiello (ligament) will be unavailable for their Champions League opener, although the latter would have never displaced Mike Maignan in goal.
German defender Malick Thiaw is also nursing an ankle sprain that is proving difficult to overcome, and his chances of a midweek comeback are slim to none, while Davide Calabria is touch-and-go after missing the Venezia thumping with a blow to his leg.
Unless any last-minute knocks force his hand, Fonseca will surely stick with the same winning formula from the weekend, as Abraham keeps new signing Alvaro Morata at bay to join fellow erstwhile Chelsea men Pulisic and Ruben Loftus-Cheek in the XI.
AC Milan possible starting lineup:
Maignan; Emerson, Gabbia, Pavlovic, Hernandez; Reijnders, Fofana, Loftus-Cheek; Pulisic, Abraham, Leao
Liverpool possible starting lineup:
Alisson; Alexander-Arnold, Konate, Van Dijk, Robertson; Endo, Gravenberch; Salah, Szoboszlai, Gakpo; Nunez
We say: AC Milan 1-1 Liverpool
Milan evidently benefitted from the two-week hiatus much more than Liverpool did based on their respective domestic displays, and the Rossoneri have also managed to avoid defeat in each of their last four Champions League games against English clubs.