The season has gone sour for both clubs recently.
Juve, winners of the last nine league titles, are at risk of a previously unthinkable failure of missing out on a top-four spot, having started the season as title favourites.
Milan, meanwhile, had Scudetto aspirations of their own after a superb start to the season kept them top of the table until February.
Now they head to Turin on Sunday for a crucial game in both sides’ quest to reach European football’s top competition next season.
“The team that loses is out,” former Juventus and Milan coach Fabio Capello told Corriere della Sera.
“It is not just about the league table. I think the psychological repercussions of a defeat would be very heavy.
“They are already not doing well, they are the two teams in most difficulty. Losing the playoff would be a blow.”
Milan bounced back from two straight defeats to beat Benevento 2-0 last weekend, while Juve struggled to a 2-1 win at Udinese.
However, both sides are lacking in form and confidence and have their fair share of off-pitch distractions to deal with.
The Turin club have struggled to find an identity under rookie coach Andrea Pirlo, resulting in incessant speculation that Massimiliano Allegri is set to replace him.
Tensions in Milan came to a head last weekend when a group of hard-line “Ultras” confronted goalkeeper Gianluigi Donnarumma, demanding that he either renews his soon-to-expire contract or does not play against Juventus. Milan subsequently froze all contract talks.
Both clubs were involved in the ill-fated European Super League project last month, a move that led to 11 Serie A clubs jointly signing a letter demanding consequences for their actions and Milan President Paolo Scaroni resigning from his position on the league council.
To make matters worse, both teams have had to watch on as their major rivals Inter Milan celebrated wrapping up the league title with four games to spare.
Five points separate Atalanta in second from Lazio in sixth with four games to go, but the Roman club have a game in hand.
Atalanta, level on 69 points with Juve and Milan, are unbeaten in eight games and travel to already-relegated Parma on Sunday.
Napoli, two points back in fifth, slipped up with a draw against Cagliari last time out but are otherwise in good form and face Spezia on Saturday.
Lazio’s 4-3 win over Genoa was their 11th home win in a row, a club record, and their seventh victory in the last eight games.
The capital club are at Fiorentina on Saturday and have a favourable run-in, making it difficult to predict the eventual top four make-up
/ 2 months ago
Et harum quidem rerum facilis est et expedita distinctio. Nam libero tempore, cum soluta...