Having been docked 10 points and dropped down to seventh place, Juve then followed their European exit with a humbling in Empoli. Milan, meanwhile, have also endured semi-final heartache of late and are still embroiled in the fight for a top-four finish.
Match preview
As if missing out on a place in the Europa League final was not enough of a blow for Juventus fans to absorb, over the past week, events involving the 36-time Italian champions have since unfolded in typically dramatic fashion.
Serie A's crisis club lurched to another low hours after having their points penalty for financial misdeeds reimposed, and a 4-1 defeat to struggling Empoli was their ninth of a miserable campaign.
After their setback at Stadio Carlo Castellani, Juventus have now lost that many times in a league season for the first time in 12 years, and Max Allegri's once-imperious position as Bianconeri boss has come under ever greater scrutiny in the aftermath.
The ex-Milan manager has presided over a second straight trophyless season in Turin - a far cry from his successful first spell in charge - and booking a Europa League return is the best his dispirited side can realistically hope for after their final two fixtures.
Heading into the penultimate weekend, Juve sit seventh - five points adrift of fourth-placed Milan, and with both Atalanta and Roma sandwiched between - so will need several results to go their way if they are to salvage something from Allegri's second year back at the Allianz Stadium.
One of the few pluses for the Old Lady this season - in addition to the blooding of several promising youngsters - has been a formidable home record in Serie A. In fact, no team have earned more points as hosts, including new champions Napoli.
By contrast, Milan - who recently had to hand over the Scudetto to their Neapolitan rivals - are ranked only ninth in terms of points earned away from home, and as a result their title defence has been hugely underwhelming.
After winning 2-0 win in October's reverse fixture, the Rossoneri now aim to defy such sub-par form on the road to do the double over Juventus for just a third time in the last 50 years - and the first since 2010.
Recent history is certainly on their side before Sunday's late kickoff, as Milan have not only kept a clean sheet in their last two league games against Juve but their last Serie A loss to them came back in January 2021.
Since then, Stefano Pioli's men have remained unbeaten in four subsequent league meetings, and having bounced back from their Champions League semi-final defeat to city rivals Inter with a 5-1 trouncing of Sampdoria last week, they will be keen to keep such a run going.
With Olivier Giroud fresh from his hat-trick heroics against Samp, and last year's Serie A MVP Rafael Leao also back in full flow following injury, Milan may now fancy their chances of success in Turin - which would also finish off Juve's dim top-four dreams.
However, the Rossoneri have won just one of their last nine away matches across all competitions - a shock 4-0 victory over Napoli at the start of April - and have lost both of the last two.
Juventus Serie A form:
L
D
W
W
W
L
Juventus form (all competitions):
W
W
D
W
L
L
AC Milan Serie A form:
W
D
D
W
L
W
AC Milan form (all competitions):
D
W
L
L
L
W
Team News
After a long absence list forced his hand in Empoli, Max Allegri will at least have both Juan Cuadrado and Danilo back from suspension on Sunday.
However, Nicolo Fagioli, Paul Pogba, Mattia De Sciglio and Juventus captain Leonardo Bonucci - who recently announced he will retire in 2024 - have all been ruled out for the season.
The subject of much transfer speculation, Dusan Vlahovic may see his unhappy first full season at the club continue, as a tendon problem has kept the Serbian striker out of training this week; Arkadiusz Milik is therefore set to lead the line.
Despite a decline in his output since the World Cup, Milan's main man up front, Olivier Giroud, has now scored 11 goals in Serie A this season - one more would see him surpass his tally from the 2021-22 campaign.
The Frenchman's fellow forward Zlatan Ibrahimovic joins Alessandro Florenzi and Ismael Bennacer on the sidelines - the latter was recently ruled out of action for several months by a serious knee injury.
Stefano Pioli's main selection headache comes in central defence, as either the vastly experienced Simon Kjaer or promising rookie Malick Thiaw will partner Fikayo Tomori at the back.
Juventus possible starting lineup:
Szczesny; Gatti, Bremer, Danilo; Cuadrado, Miretti, Locatelli, Rabiot, Kostic; Di Maria; Milik
AC Milan possible starting lineup:
Maignan; Calabria, Tomori, Thiaw, Hernandez; Tonali, Krunic; Messias, Diaz, Leao; Giroud