Arne Slot's side are looking to bounce back from a shock 1-0 defeat to Nottingham Forest at Anfield over the weekend by claiming three points in their first game back in the Champions League.
European away days do not get quite as big as a trip to the Rossoneri though, as the two will face off in a repeat of the 2005 and 2007 finals.
Milan are not at the level they were at during those days of success in 2000s though, and Paulo Fonseca's side are not exactly brimming with confidence after a slow start to the season.
Bennacer ruled out of Milan-Liverpool clash
News of Bennacer's setback has come via an official club statement, which reveals the midfielder will miss around four months of action.
After picking up an issue while on international duty with Algeria, Bennacer flew to Finland to have surgery on his calf, which was successful.
Fonseca will be without the 26-year-old until the new year though, having only been able to call on him from the start once so far this season.
The Algerian missed Milan's final game before the international break, but was available to represent his country against Equatorial Guinea, before breaking down once more.
Bennacer is a player who has been struck down by injury numerous times during his spell at San Siro, as he only managed to play 20 Serie A matches last season.
More bad news after a difficult start for Fonseca
News of Bennacer's lengthy setback will not be welcomed by manager Fonseca, who has endured a difficult spell in his opening month in charge of the Rossoneri.
Replacing Scudetto-winning manager Stefano Pioli was no easy task, but after being given a relatively kind start fixture-wise, Milan had to wait until matchday four for their first win.
After taking just two points in their opening three games versus Torino, Parma and Lazio, fan protests took place prior to the weekend fixture with Venezia.
While Milan would go on to thrash the newly-promoted side 4-0, easing tensions for now, that can quickly turn again should results go in the opposite direction once more.
Venezia were a side they were fully expected to beat, now Milan must show they can be competitive in the Champions League, something they have not been able to do for the best part of 15 years, apart from their one semi-final appearance in 2023.