Franck Kessie was sent off as AC Milan lost 2-1 to Atletico Madrid in Tuesday's Champions League encounter.
A minute before the half hour mark of the Group B fixture, the Cote d'Ivoire international was given the marching orders for a second caution by referee Cuneyt Cakir.
Kessie, 24, had already been cautioned in the 15th minute for a foul on Marcos Llorente, however, he was shown the way out fourteen minutes later for another bookable offence against the Spaniard.
That is the first time the former Atalanta man would be shown a red card in the competition and the fourth in his professional career so far.
Also, the Cote d'Ivoire international became the first AC Milan player to be dismissed in the Champions League since Riccardo Montolivo in December 2013 against Ajax, while only Roque Junior (24y 167d) was sent off for the Red and Blacks in the tournament at a younger age than Kessie (24y 283d).
Having in mind that the winners of the crunch tie would revive their hopes of qualifying for the next round after a mumbling start, both clubs came to the San Siro with all guns blazing.
Nevertheless, it was the Italians who took the lead in the 20th minute as Rafael Leao slotted Brahim Diaz's pass beyond goalkeeper Jan Oblak.
With the home team reduced to ten men, the La Liga side dominated ball possession and could have restored parity on the stroke of half time, but Luis Suarez volleyed inches wide from close range.
Despite playing with a man less, Stefano Pioli's men adopted a more defensive approach towards preserving their lead, albeit, the Spaniards continued to make extra man count.
In the 84th minute, Diego Simeone's team eventually got the breakthrough as Antoine Griezmann snuck in front of Alessio Romagnoli before striking past goalkeeper Mike Maignan.
With the game looking destined to end on a no winner, no vanquished note, DR Congo prospect Pierre Kalulu was adjudged to have handled the ball inside the penalty area and Suarez smartly converted the ensuing penalty.
Central African Republic international Geoffrey Kondogbia was named in Atletico Madrid's starting XI, but he was subbed off for Thomas Lemar in the 64th minute.
AC Milan would be hoping to bounce back from this setback when they travel to FC Porto on October 19.