AC Milan suffered an embarrassing exit from the Coppa Italia as they were beaten 1-0 in extra time by a Torino side who played over 50 minutes with ten men.
After throwing away a two-goal lead against Roma at the weekend it was important for a response to arrive under the lights of San Siro, but it was yet another abject and worrying performance as Milan failed to score in 120 minutes of action.
When Djidji saw red with a large chunk of normal time remaining it seemed as though the Rossoneri would be able to make their numerical superiority and dominance pay, but it was a sucker punch on the counter in the second half of extra time that saw Ivan Juric’s men through.
Stefano Pioli opted to field a somewhat experimental line-up with Matteo Gabbia, Pierre Kalulu and Fikayo Tomori in a back three, Alexis Saelemaekers and Sergino Dest as wing-backs, Aster Vranckx, Sandro Tonali and Tommaso Pobega in midfield and Charles De Ketelaere joined up front by Brahim Diaz.
The opening 10 minutes of the game passed virtually without incident as the two sides felt each other out in a very cagey beginning to the match.
Torino had the first big opportunity of the game as the run of Sasa Lukic from midfield was not followed by anyone and the Serbia international got off a low shot inside the box that Ciprian Tatarusanu did well to save.
Milan were very close to taking the lead bang on 25 minutes after another passage in which very little happened. A period of pressure on the edge of Torino’s box ended with Dest unleashing a shot that deflected up into the air and almost beat the back-peddling Milinkovic-Savic yet he tipped it over the bar.
From the resulting corner the Rossoneri were even closer to going a goal up as a whipped delivery to the near post was glanced towards the far corner by De Ketelaere, but such is his luck at the moment that it hit the inside of the post and bounced clear.
Milan continued to exert pressure during the final stages of the first half, with Dest slashing a half volley over the bar from the edge of the box and then De Ketelaere being denied from a similar range with a shot that was straight at Milinkovic-Savic.
There were a couple of half chances for both sides in the opening exchanges of the second half as Torino first flashed a low ball across goal that was asking for a touch, and at the other end Pobega flicked a feed from Dest into the air and acrobatically fired an effort towards goal that was rather comfortably parried away.
The Rossoneri continued to probe the visitors’ defence, and a couple of corners in quick succession in the 55th minute ended with Tonali slashing an effort wide after a lay-off from Pobega.
Shortly after Torino had a good spell of pressure themselves, Pioli decided to make a double change midway through the second half as Junior Messias and Rafael Leao came on for Saelemaekers and Brahim Diaz.
Messias almost made an instant impact as a brilliant ball over the top from Tonali found the run of the Brazilian who lofted an effort over Milinkovic-Savic from a narrow angle but ultimately past the far post.
A huge moment came in the 70th minute as Messias looked to burst through on goal after a Torino corner was cleared, but Djidji brought him down and was shown a yellow card, which was his second and thus a red followed.
A couple of changes came with just less than 15 minutes on the clock as Pioli looked to get the job done in normal time, with Theo Hernandez and Olivier Giroud coming on for Gabbia and Pobega.
A final substitution was made inside the final 10 minutes as Ismael Bennacer came on for Vranckx, just after Theo Hernandez had fiercely struck a half volley that at Milinkovic-Savic from 20 yards out.
The Torino keeper was called into action in the second of five added minutes to tip a Theo Hernandez shot wide of the post, though it was going wide anyway.
Milan as expected piled on the pressure early in extra time and should have probably taken the lead when a corner found Leao at the far post whose low effort deflected towards three Rossoneri players who were a few yards out yet none of them reacted in time to steer it in.
The two sides traded chances as tired legs began to show, with Dest having a low shot through a crowd well saved and Linetty blazing over at the other end, providing a reminder of the dangers of committing too many men forward.
The opportunities continued to come as a deflected cross from Leao was brought down by Giroud deep inside the area but again Milinkovic-Savic was equal to the attempt.
A sixth substitution (one extra becomes available in extra time) was made with 10 minutes to go as Davide Calabria came on for Dest.
Just as it seemed likely that Torino might settle for penalties, they went up the other end and scored with a devastating counter-attack. Two substitutes combined as Bayeye was set free down the right flank and he served a perfect feed to Adopo who finished from close range with six minutes left on the clock.
In the end that would be enough to secure progression into the last eight of the competition for the Granata, who face the winner of Fiorentina against Sampdoria.