Following successful forays into Europe during the week, both sides are well poised for an absorbing encounter, contesting a fixture rich in history and tradition.
Only three times in an illustrious history have the Rossoneri won their opening five matches in a Serie A season, doing so most recently during the halcyon days of 1992-93. Monday's test will be one of their firmest yet, though, as they take on a Roma side boasting three wins on the spin.
Stefano Pioli's remarkable transformation of a loose collection of under-performing individuals into a well-oiled winning machine has been as remarkable as it was unexpected.
No team has won more matches than Milan across the 'top five' European leagues since football restarted post-lockdown - 13 in total, alongside Real Madrid. With 16 so far, the Rossoneri have also played the most games in this period without suffering a loss.
Their recent record against their southern counterparts is good too: Milan have won their last two home league games against Roma. The last time the Rossoneri won three consecutive matches against the Giallorossi at San Siro was back in 1996, under the guidance of a legendary figure at both clubs, Fabio Capello.
Zlatan Ibrahimovic netted a crucial double in last week's Derby della Madonnina, breaking his former club Inter's long unbeaten run in that iconic contest. The talismanic forward, largely responsible for unifying and inspiring those around him, has netted a brace in each of his last two matches against Roma too.
Success at Celtic Park on Thursday saw a side featuring several changes take care of business against the Scottish champions; fringe players such as Rade Krunic, Jens Petter Hauge - recently signed from previous Europa League opponents Bodo Glimt - and Manchester United loanee Diogo Dalot taking their opportunity to impress with both hands.
Roma also thrived on the road, beating Young Boys in Switzerland to get off to a flying start in Europe's secondary competition. With seven points from the last three league games too, Paulo Fonseca's side are fast making up ground lost on their fellow top four contenders.
Key men have been playing themselves into form for the Giallorossi: Pedro has scored in each of his last two Serie A games, while Jordan Veretout has scored five goals in his last six - four of those coming from the penalty spot.
Crucially, the focal point of all their attacking play, Edin Dzeko, whose start to the season was badly disrupted by the endless transfer market machinations surrounding him, registered a double in their last league game, a 5-2 victory over Benevento.
Last season, Milan won this fixture 2-0, thanks to goals from Ante Rebic and Hakan Calhanoglu. That pair have enjoyed their best form at the club in recent months, but neither may be fit to start Monday's clash.
Nonetheless, with a squad now brimming with talent and potential, the league leaders look in excellent shape to face down one of their closest rivals in the race to end Juventus' domestic dominance.
AC Milan Serie A form: WWWW
AC Milan form (all competitions): WWWWW
Roma Serie A form: LDWW
Roma form (all competitions): LDWWW
Roma chief Paulo Fonseca finds himself potentially without two key central defenders, as Chris Smalling has failed to recover from a knee sprain and Gianluca Mancini tested positive for COVID-19 earlier this week, though that has since been confirmed as a 'false positive' result.
Guniean midfielder Amadou Diawara is also out, as he continues to observe quarantine rules.
Fonseca reverted to 4-2-3-1 against Benevento last week, which may be the case again in Smalling's absence. That would allow Lorenzo Pellegrini to continue in an advanced midfield role.
For the home side, Rebic has not recovered from an elbow injury and is expected to remain on the sidelines, though Stefano Pioli hopes Calhanoglu, who links up so well with Zlatan Ibrahimovic, can recover to at least play a part from the bench: the gifted playmaker picked up a sprained ankle last week. Krunic and Brahim Diaz are on standby to fill in.
AC Milan possible starting lineup:
Tatarusanu; Calabria, Kjaer, Romagnoli, Hernandez; Kessie, Bennacer; Saelemaekers, Diaz, Leao; Ibrahimovic
Roma possible starting lineup:
Mirante; Fazio, Kumbulla, Ibanez; Santon, Pellegrini, Veretout, Spinazzola; Mkhitaryan, Pedro; Dzeko
We say: AC Milan 1-1 Roma
Milan's golden run must come to an end at some point, as they start to encounter tougher opponents - perhaps Monday will be the day.
Though a prime example of inconsistency in recent months, Roma visit San Siro with their key men coming into form and on the back of three successive wins. Therefore, they can bring a point back down South and stop their rivals stretching away at the top of the early league table.