Milan lost the derby on Monday, a defeat which allowed Inter Milan to clinch the league title with five games still to play. Now Milan, 17 points behind Inter, are left with only a fight to maintain second place to play for.
Juventus, in third and five points off Milan, do have a Coppa Italia final to look forward to, but it has proved to be a disappointing season for both clubs, and their coaches, Stefano Pioli and Massimiliano Allegri, could pay the price.
Pioli led Milan to their first Scudetto in over a decade two seasons ago. That success gave him enough credit to overcome last season's fourth-placed finish, but his position is now very uncertain after another trophyless campaign.
Milan have lost both games with Inter this season and were beaten at home by Juventus when they met in October, and another defeat to a main rival would only put further pressure on the coach.
Pioli's side failed to make it past the Champions League group stage, and their recent exit from the Europa League at the hands of fellow Italians Roma has turned even more fans against the idea of sticking with the manager next season.
That defeat to Inter brought further problems for Milan's boss, with defenders Davide Calabria, Theo Hernandez and Fikayo Tomori all suspended for the trip to Juventus on Saturday.
A Milan win, or even a draw, would probably be enough at this stage for Pioli to hold on to second place, but holding on to his job may prove a more difficult task.
Allegri's first spell at Juventus brought five consecutive league titles, but in the three seasons since his return, they have yet to lift a trophy, and even an eventual Coppa Italia win may not guarantee his future at the club.
While a win at home to Milan on Saturday would take them to within two points of second spot, defeat could see them slip to fourth, with Bologna just two points adrift.
Bologna's impressive season looks set to bring Champions League football to the club for the first time. They beat fellow challengers Roma 3-1 on Monday and host relegation battling Udinese on Sunday.
Roma, fifth in the standings, are at defending champions Napoli on Sunday. Napoli face a battle to qualify for Europe next season, with last weekend's defeat at Empoli leaving them in eighth place.
Inter, with the title already wrapped up, can still beat their record points haul in Serie A. When Inter, who host Torino on Sunday, won the Scudetto in 2007 they collected 97 points and with five games remaining they have 86 points.
