Zlatan Ibrahimovic's landmark Serie A goal was the only highlight of a poor display for Milan as they were beaten 3-1 at Udinese on Saturday.
On his first start since January 2022 following his recovery from a knee injury, Ibrahimovic became the oldest goalscorer in Serie A history, overtaking Milan legend Alessandro Costacurta.
The 41-year-old converted a penalty at the second attempt in first-half stoppage time, cancelling out Roberto Pereyra's opener at Stadio Friuli, yet Udinese nevertheless went into the break with the lead thanks to Beto's effort two minutes later.
Kingsley Ehizibue added a third in the 70th minute, sealing eighth-placed Udinese's first home league win since they defeated Inter in September.
Udinese took the lead after just nine minutes when Ismael Bennacer's pass was intercepted after Fikayo Tomori was caught napping - Lazar Samardzic teeing up Pereyra, who rolled the ball into the far corner.
Milan were given a golden chance to equalise just before half-time though when Jaka Bijol was judged to have handled the ball in as he tried to dispossess Rafael Leao in Udinese's area.
Marco Silvestri initially saved well from Ibrahimovic's penalty down to his left, but Beto's encroachment handed the Sweden forward another chance, and he duly smashed straight down the middle.
Beto swiftly made amends, though, benefiting from Isaac Success' fine work to restore the hosts' lead.
Milan's comeback hopes were dented further when Ehizibue turned the ball in from Destiny Udogie's mishit shot.
Rade Krunic lashed over from Milan's best subsequent chance, as their rough form continued.
Medvedev battles into French Open second round after Koepfer triumph
Daniil Medvedev staved off a Dominik Koepfer fightback to record a battling victory in the French Open first round on Monday.
The world number five raced out the blocks on Court Simonne-Mathieu and eventually triumphed 6-3 6-4 5-7 6-3 in Paris.
Medvedev, a five-time major runner-up and 2021 US Open champion, broke Koepfer's first service game in the French capital with that a seeming sign of things to come.
Though the 28-year-old dropped his serve in the first set, Medvedev had little trouble in responding with the score finely poised at 3-2 to claim first blood at Roland-Garros.
The fifth seed has only ever gone as far as the quarter-finals, three years ago, at the French Open but showed his clinical best to snatch the second set after holding all six service games for a narrow triumph.
World number 65 Koepfer battled back in the third but the resilient Medvedev responded by breaking his German opponent early in the fourth set, finally securing victory in just over three hours.
Data Debrief: Medvedev gets better of Koepfer again
Medvedev has won all four of his meetings with Koepfer, with his most recent such victory seeing him reach the second round at Roland-Garros for the third time in eight attempts.
Since the start of the 2021 season, Medvedev is 27-1 against players ranked outside the top 50 at major events, with his only loss in that run coming against Seyboth Wild in the French Open first round last year.
Koepfer, meanwhile, extends to 1-17 against top-10 players in his career, earning his only such victory against over Gael Monfils – then ranked ninth in the world – at the 2020 ATP Masters 1000 event in Rome.
Euro 2024 absence caps cruel period for Netherlands midfielder De Roon
Netherlands will be without Marten de Roon at Euro 2024 after an injury blow capped a cruel period for the Atalanta midfielder.
De Roon suffered a muscle injury two weeks ago in Atalanta's 2-0 Coppa Italia final loss to Juventus, subsequently missing Gian Piero Gasperini's side lifting the Europa League with victory over Bayer Leverkusen.
The Netherlands international was in the stands in Dublin for the 3-0 win over Xabi Alonso's Bundesliga champions that secured Atalanta's first European trophy in history.
Having already been named in Ronald Koeman's 30-man provisional squad for the Euros in Germany, starting in June, De Roon suffered another gut-wrenching punch after his absence was confirmed.
"I can't imagine I've had a week in my career, or in my life, that has had so many ups and downs," the Atalanta man wrote on social media on Monday.
"Lost the Coppa Italia, couldn't play the final, win the Europa League.
"In that last euphoric state, I spent a lot of time with the medical staff: it turns out I can't play the Euros.
"I will get over it, I will watch the squad and my friends as a fan, but for now it's a very tough day."
De Roon has won 42 caps for his country and featured at the last European Championships and the 2022 World Cup in Qatar.
His absence means Koeman has to cut just six players down from his provisional squad for the final 23-man selection, which will be announced on Wednesday.
Netherlands open their Euro 2024 campaign against Poland on June 16 before facing France and Austria in the group stages.
Koeman's squad assembled on Monday for their pre-tournament training camp, ahead of warm-up matches with Canada and Iceland.
Al-Nassr 4-2 Al-Ittihad: Ronaldo breaks Saudi Pro League scoring record in final-day win
Cristiano Ronaldo claimed a piece of Saudi Pro League history after scoring twice in Al-Nassr's 4-2 final-day victory over 10-man Al-Ittihad on Monday.
The five-time Ballon d'Or winner was on target in either half at Al Awal Park, moving to 35 goals across the 2023-24 league campaign in Saudi Arabia.
Ronaldo opened the scoring on the stroke of half-time after receiving a long ball from Mohammed Al-Fatil, before doubling his tally – and Al-Nassr's lead – with a header from Marcelo Brozovic's corner.
That second finish after Suwailem Al Manhali was dismissed for the visitors saw Ronaldo eclipse Abderrazak Hamdallah's 34-goal tally – in the 2018-19 season – for the most strikes in a single campaign.
Abdulrahman Ghareeb then added another from the penalty spot before Meshari Al Nemer made sure of three points after late goals from Farhah Al Shamrani and Fabinho had pulled Al-Ittihad back into contention.
Having already been unable to stop Al-Hilal secure the title, Al-Nassr finish second in the table – ending on 82 points after 26 wins from the 34-match campaign.
Data Debrief: Al-Nassr dominance pays off
Much will be made of the record-breaking Ronaldo, who has scored 50 goals in as many games across all competitions this season.
Yet Al-Nassr were dominant from the off in this one, mustering nine shots on target to Al-Ittihad's three, while accumulating 2.73 expected goals (xG) – far superior to the visitors' 1.43 xG.
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