AC Milan's Zlatan Ibrahimovic became the oldest goalscorer in Serie A history but it was not enough to prevent them suffering a 3-1 loss at Udinese on Saturday in a blow to the defending champions' hopes of securing a top-four finish.
Milan missed the chance to jump to second and remained fourth with 48 points, a point clear of fifth-placed AS Roma, who play Lazio on Sunday.
Udinese took the lead after nine minutes when Lazar Samardzic intercepted a poor pass from Ismael Bennacer in midfield and surged forward into the box, where Roberto Pereyra latched onto the ball and slotted it into the right corner.
It took Milan 20 minutes to get a foothold in the match after the hosts had taken an aggressive approach from the first whistle, creating several chances to double their lead.
It was Milan who struck next however, albeit in confusing circumstances.
Milan striker Ibrahimovic first missed a penalty after a handball late in the first half, before it was ordered to be retaken due to encroachment after play had already continued for a minute. Udinese coach Andrea Sottil was sent off after verbally abusing the referee following the decision.
Ibrahimovic, who was starting his first game since January 2022, did not miss a second time, converting four minutes into first-half stoppage time, to become the oldest goalscorer in Serie A history at 41 years and 166 days.
He surpassed the previous record set by Alessandro Costacurta in 2007 by 141 days. Costacurta also scored his last goal from the penalty spot for Milan in a defeat against Udinese.
The celebrations were short-lived, however, as Beto put Udinese back ahead two minutes later when he converted an Isaac Success cross from close range.
Udinese made sure of the win when an unmarked Kingsley Ehizibue tapped in a pass from Destiny Udogie at the back post in the 70th minute.
The win maintained Udinese's hopes of playing in Europe next season, as they moved up to eighth place, seven points behind Atalanta in sixth, the last qualification place.