Dortmund top Group F on seven points following back-to-back victories over Newcastle United, while third-placed Milan sit just two points behind after toppling Paris Saint-Germain earlier this month.
Match preview
With qualification for the Champions League's last 16 to be decided over the last two matchdays, a quartet of clubs are separated by just three points heading into the penultimate round of Group F fixtures.
After battling back from behind to beat Paris Saint-Germain earlier this month, when goals from Rafael Leao and Olivier Giroud secured maximum points, Milan know another victory at San Siro would leave them within touching distance of making the knockout phase in consecutive campaigns.
While that will be far from a straightforward task against in-form Dortmund, last season's semi-finalists - who had lost 3-0 to PSG in France - now have their destiny in their own hands: back-to-back victories over the German giants and then Newcastle would guarantee a top-two finish.
The Rossoneri recently returned from a welcome international hiatus having taken just two points from their previous four domestic matches, with an unpredictable Fiorentina side providing their opposition on Saturday evening.
Hit by absences up front, 15-year-old forward Francesco Camarda became the youngest player in Serie A history upon his arrival from the bench, as Milan edged to a 1-0 win over the Viola thanks to a Theo Hernandez spot-kick just before the break.
With Giroud and Leao both unavailable, Stefano Pioli's side were unable to find the net in open play, and as they have only scored twice in four Champions League matches this season, concerns remain about their relative lack of attacking prowess.
Now set to host Borussia Dortmund in Europe's top club tournament for the first time since a 1-0 defeat in the 2002-03 campaign, Milan have lost just one of their last 16 home games against German opponents in UEFA competition, winning 11 times in the process.
After they most recently met Milan, in last month's goalless draw on home turf, Dortmund's tally of one point from their first two matches left the Bundesliga side staring at an early exit.
BVB have since turned things around, however, and they reached the Group F summit thanks to back-to-back victories over Newcastle - most recently winning 2-0 in Germany to take charge of their own fate.
Niclas Fullkrug and Julian Brandt struck in either half to secure maximum points against the Magpies, and for the first time in their history, Dortmund have gone four straight Champions League home matches without conceding a single goal.
Now looking to win three consecutive games in the competition for the first time since 2020, Die Schwarzgelben will travel to Italy's second city amid some inconsistent form on the domestic scene, where they sit 10 points off the relentless pace set by league leaders Bayer Leverkusen.
Following a 4-2 defeat of Borussia Monchengladbach at the weekend, in which Germany striker Fullkrug was on target again as BVB battled back from two goals down, head coach Edin Terzic has overseen only three losses in 18 games this term; however, his team have been short of their former fluency up front.
Taking just one point from three Bundesliga fixtures before the international break saw Dortmund slip further behind in the title race, but making progress in Europe would certainly polish their credentials and give them plenty to look forward to in 2024.
AC Milan Champions League form:
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AC Milan form (all competitions):
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Borussia Dortmund Champions League form:
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Borussia Dortmund form (all competitions):
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Team News
Having tarnished his 100th Milan appearance by being sent off against Lecce earlier this month, Olivier Giroud can now return to the Rossoneri's starting XI after serving a Serie A suspension against Fiorentina.
Such a boost will be welcomed by Stefano Pioli, who remains without two other forwards, Noah Okafor (hamstring) and Rafael Leao (thigh), due to injury.
Luka Jovic and Samu Chukwueze both stepped in alongside Christian Pulisic on Saturday, but with Giroud available, Jovic should drop down to the bench. Chukwueze may be retained, as Leao - top of Milan's Champions League rankings for chances created from open play (eight) and dribbles completed (15) - misses out again.
After Ruben Loftus-Cheek, who played starring role against PSG, made his Serie A comeback as a substitute at the weekend, the English midfielder will be in contention to start on Tuesday.
One of only three players in double figures both for tackles and interceptions in this season's Champions League - another being Milan's Fikayo Tomori - veteran defender Mats Hummels will helm Borussia Dortmund's back four at San Siro.
The visitors will be without Felix Nmecha, whose hip injury recently ruled him out of the Germany squad, but Emre Can and Gregor Kobel both overcame fitness concerns to face Gladbach.
Leading the line up front, Niclas Fullkrug has scored in his last three outings for BVB, while Donyell Malen should force his way past Jamie Bynoe-Gittens to start in support of Dortmund's frontman. Fellow forwards Karim Adeyemi and Sebastien Haller have been laid low by illness.
AC Milan possible starting lineup:
Maignan; Calabria, Tomori, Thiaw, Hernandez; Musah, Reijnders; Chukwueze, Loftus-Cheek, Pulisic; Giroud
Borussia Dortmund possible starting lineup:
Kobel; Sule, Hummels, Schlotterbeck, Ryerson; Can, Sabitzer; Reus, Brandt, Malen; Fullkrug