Milan came back from 2-0 down after Luka Jovic saw red with Olivier Giroud and Christian Pulisic, but Monza made it 4-2 in stoppages with Warren Bondo and Lorenzo Colombo.
The Rossoneri were coming off Thursday’s 3-0 Europa League win over Rennes and knew a win would allow them to leapfrog Juventus into second, but made six changes including the return of Malick Thiaw for his first start since pulling his hamstring on November 28. Davide Calabria, Fikayo Tomori, Pierre Kalulu and Tommaso Pobega were out of action, while the hosts missed Patrick Ciurria, Gianluca Caprari and Samuel Vignato, moving to a 4-2-3-1 formation to mirror their opponents.
This will always be a special fixture, as the two clubs shared the love of President Silvio Berlusconi, who died in June 2023, and CEO Adriano Galliani.
Luka Jovic’s header was straight at Michele Di Gregorio after 80 seconds, then Theo Hernandez had a shot deflected wide after good work from Samuel Chukwueze.
The Nigeria international, on his return from AFCON duty, also fired straight at the goalkeeper, while Ismael Bennacer slipped at the last moment after a strong run forward.
Monza had the best opportunity, as Milan Djuric was facing the wrong way, but with a flicked header managed to steer the Valentin Carboni cross onto the woodwork at the near top corner.
There was a nasty collision between teammates Andrea Carboni and Di Gregorio, leaving both in need of bandages for cuts to their heads. The goalkeeper came off worse, was feeling dizzy and had to be replaced by Andrea Sorrentino.
Moments later, Thiaw marked his comeback with a huge mistake, as he already tried to trip Djuric outside the area, the referee played the advantage and he then brought down Dany Mota Carvalho as well for an inevitable penalty. Matteo Pessina converted after a stuttering run-up to send Mike Maignan to ground.
Milan had a double chance to equalise before half-time, but the acrobatic Jovic half-volley was charged down by Pablo Mari, then Theo Hernandez blasted the rebound over.
Instead, Monza added a second moments later with a classic counter-attack. Andrea Colpani robbed Bennacer down the right, nutmegged Thiaw and rolled across for Dani Mota Carvalho, who cut inside Alessandro Florenzi to curl right-footed into the far top corner from 14 yards.
Sorrentino used his legs to parry the deflected Florenzi free kick on the stroke of half-time after nine minutes of stoppages, awarded for those two head injuries.
Stefano Pioli threw on Rafael Leao, Christian Pulisic and Tijjani Reijnders for the restart, but things went from bad to worse when Milan were reduced to 10 men.
The referee had only just warned Jovic and Armando Izzo not to keep tussling when 10 seconds later he booked Jovic for flailing an arm out on Izzo’s face. However, following the VAR on-field review, he changed that to a red card, as the striker had slapped his opponent in this off the ball incident. It was the sixth dismissal of the season for Milan, more than any other club.
Pulisic’s pull-back from the by-line for substitute Olivier Giroud was crucially intercepted, then Izzo made the decisive block from six yards on Rafael Leao after a well-worked move from right to left.
Colpani really should’ve made it 3-0 only to turn a free header wide at the back post on the Dany Mota cross, but instead Milan got back into it with 10 men.
A cross from the right was flicked on by Pulisic for fellow substitute Giroud to acrobatically volley in at full stretch from close range.
Florenzi’s scorcher from distance flashed wide, Samuele Birindelli stung Maignan’s gloves at the near post and Ruben Loftus-Cheek nodded into the arms of Sorrentino.
Matteo Gabbia made a decisive block on Pedro Pereiro in a four on three counter-attack, but Milan completed the comeback from 2-0 down to 2-2 down to 10 men when Pulisic cut inside the right side of the box and bent a perfect left-foot finish into the far top corner.
However, as Milan tried to go on and win it, they were caught out for a third time. Daniel Maldini – on loan from the Rossoneri – controlled a Pessina cross-field pass and laid it off for the spectacular Warren Bondo strike into the far top corner from the edge of the area. The offside flag went up, but VAR over-ruled it.
It still wasn’t over, as Pessina sent Lorenzo Colombo down the right and the striker owned by Milan drilled his finish between Maignan and the base of the near post.
Monza 4-2 Milan
Pessina pen 45 (Mo), Mota Carvalho 45+6 (Mo), Giroud 64 (Mi), Pulisic 88 (Mi), Bondo 90 (Mo), Colombo 95 (Mo)
Sent off: Jovic 52 (Mi)
