In what is shaping up to be a classic Coppa Italia semifinal, the matchup of resurgent AC Milan and Juventus centers around a duel between two of the most influential and often controversial goal-scorers not only in Italy, but in the world — Milan's Zlatan Ibrahimovic, and Juve's five-time Ballon D'or winner, Cristiano Ronaldo. With Ibra arriving on a free transfer from the MLS team L.A. Galaxy, Milan has won three of five — while Ronaldo still has "The Old Lady" well-positioned for a ninth Serie A title in a row, level on points with Inter Milan.
But both teams enter the first leg of the Cup semifinal coming off of deflating defeats in league play. On Saturday, Juventus was stunned 2-1 by mid-table Hellas Verona. And then on Sunday, in the 226th Derby Della Madonnina, AC Milan watched helplessly as a 2-0 halftime lead over crosstown-rivals Inter blew up in their faces, turning into a 4-2 defeat.
As heated as the Milan intra-city rivalry may be, however, AC Milan and Juventus have actually faced each other more times, historically. The two sides have squared off on 230 occasions, according to Sportskeeda, with Juventus winning 91, to 66 for the Rossoneri.
But AC Milan have not seen a win in the classic fixture since 2016.
ESPN FC previews the Ibra-Ronaldo confrontation in the video below.Before Inter absorbed a loss in their first-leg Coppa Italia semifinal on Wednesday, allowing a crucial away goal in the 1-0 defeat to Napoli, they were installed as second-favorites to win the Cup, at moneyline odds of +350, according to odds posted by Sports Betting Dime. In other words, a wager of $100 on Inter to win it all would return $350 plus the original $100 bet.
But Juventus remain the runaway favorites at -110. That is, a $110 bet pays only $100 profit. Napoli enjoy odds of +350, while AC Milan are the longshots at +900 to win the Cup.
In terms of odds for Thursday's first-leg matchup, Juventus have as expected been set as the favorite, according to the odds published by Goal, with even-money decimal odds of 2.0. Underdog Milan have been given decimal odds of 3.60, which translates to fractional odds of 13/5 to win the match.
Odds of a draw have been set at 3.50, or 5/2, according to Goal.com.
Not only have AC Milan failed to defeat Juventus in almost four years, in their last five matches against the 35-time champions, they have managed to find the back of the net on just one, lone occasion.
The AC Milan vs. Juventus Coppa Italia match is scheduled to kick off at 8:45 p.m. Central European Time at the legendary San Siro Stadium in Milan, on Thursday. In the United States, that start time converts to 2:45 p.m. EST, 11:45 a.m. PST, and the online streaming sports service ESPN+ will be the only outlet to carry the game.