Milan failed to move back within three points of Serie A leaders Napoli as goals from Koffi Djidji and Aleksey Miranchuk condemned the Rossoneri to a surprise 2-1 loss to Torino.
Miranchuk followed up Djidji's glancing header with a cultured left-footed finish as Torino scored twice in two frantic first-half minutes to stun Milan at the Stadio Olimpico Grande Torino.
Stefano Pioli's men travelled to Turin looking to stay within touching distance of the Serie A summit, but were uncharacteristically lethargic for long periods on Sunday.
Junior Messias was gifted a goal following a bizarre mix-up at the back, but Milan failed to build on that strike late on as Torino clung on for a huge win.
Rafael Leao missed two golden chances in the first six minutes, sending a wild volley over after breaking in behind before mishitting his shot after being teed up by Brahim Diaz.
Torino punished Milan for their wastefulness 10 minutes before the break, as Djidji nodded Valentino Lazaro's deep free-kick in off the right-hand post.
Things quickly went from bad to worse for the champions as Miranchuk latched onto Nikola Vlasic's knock-down before shifting the ball onto his left foot and finishing coolly across Tatarusanu.
Sergino Dest fired over from range as Milan attempted to lift the tempo after the break, before Messias ensured a tense finish when he curled home following a clash between Vanja Milinkovic-Savic and Perr Schuurs.
Torino boss Ivan Juric was dismissed for berating referee Rosario Abisso following that goal, but his team showed greater composure to see out the closing stages in relative comfort.
What does it mean? Rossoneri fall short
Although the likes of Napoli and Atalanta have made headlines in Serie A by emerging as surprise pacesetters, Milan had begun their title defence in solid fashion, stretching their unbeaten away run to 17 league games ahead of Sunday's contest (W12 D5).
Milan had also kept five consecutive clean sheets in league meetings with Torino prior to this game, but they saw both of those records fall by the wayside after a quickfire double from their hosts, who richly deserved the win following a disciplined performance.
Djidji ends barren run
To say Torino have struggled against Milan in recent meetings would be an understatement: Djidji's opener ended a 499-minute run in which Torino had failed to find the net against Milan in Serie A meetings.
Their previous goal against the Rossoneri in the competition was scored by Andrea Belotti in September 2019, and prior to Sunday's game, no player in Torino's current squad had scored a league goal against Milan.
Leao kept quiet
Leao has emerged as the most obvious goal threat in an exciting Milan team, having recorded nine league goal contributions (five goals, four assists) ahead of the trip to Turin.
However, the Portugal attacker was hauled off at the break after a disappointing first half in which he squandered chances amounting to 0.51 expected goals (xG) and failed to hit the target with any of his four attempts.
What's next?
Milan host Salzburg in the Champions League on Wednesday, needing to avoid defeat to reach the last 16. Torino, meanwhile, go to Bologna in Serie A next Sunday.
Howe taking plenty of positives despite frustrating Newcastle campaign
Eddie Howe was keen to look at the positives after Newcastle United secured seventh place in the Premier League on Sunday.
Alexander Isak and Bruno Guimaraes were among the goalscorers as Newcastle won 4-2 at Brentford to finish their Premier League campaign.
The victory ensured a seventh-place finish, and a Manchester City victory over Manchester United in next Saturday's FA Cup final will confirm Newcastle's place in next season's Europa Conference League.
While this season did not quite live up to the heroics of last term, which saw the Magpies finish in the Champions League spots, Howe still feels it has been a successful campaign.
"It summed up our season," Howe told BBC Sport. "We weren't totally secure at the back, but great credit to the players. They've done their job - now we wait and see.
"We anticipated after losing against Manchester United that our control of the [European] situation had gone. It's never a nice situation, but whatever happens, happens.
"We have issues to solve defensively. If we can do that, next season could be another season of really strong performances. This was a season that could have been better, but a good season overall.
"We're a really united club. I think we're still moving forward, so there's a lot to be positive about."
Postecoglou will not settle until Tottenham hit his 'lofty ambitions'
Ange Postecoglou warned Tottenham he will not settle until the club hits the "lofty ambitions" targeted in his mind.
Spurs were 3-0 victors over Sheffield United at Bramall Lane on Sunday, ending their Premier League season with a convincing win to finish fifth in the table.
Postecoglou voiced his frustrations after Tuesday's 2-0 defeat to Manchester City ended their hopes of Champions League football next term.
The Spurs head coach was far more relaxed after his side performed well in Sheffield, with Dejan Kulusevski twice on target, along with a goal for Pedro Porro against the relegated Blades.
Yet Postecoglou insisted his ambitions remain high as the Australian attempts to take Tottenham to the next level.
"Contrary to my general demeanour, I have loved every minute of it," former Celtic boss Postecoglou said of his first season in charge of Tottenham.
"It is a great challenge in the Premier League and taking over a big club that didn't have a great year last year. You understand it is not going to run smoothly, but I have enjoyed the whole season.
"I have got some lofty ambitions for the football club and until we reach that point I am not going to be smiling too much.
"As I said, all any manager wants is maximum effort and I have got that from everyone involved. I have enjoyed it and looking forward to pushing on from here."
Asked to summarise his first campaign in England's top league, Postecoglou continued: "It's been good, it's been eventful, it's had a bit of everything.
"I am obviously not delighted with the way we finished the season but in fairness to the players and staff we have been in the top five all season, in a year where there was a fair bit of upheaval.
"We finished eighth last year, player turnover, different football, different way of training, it is not easy to maintain a level when you are trying to do that.
"Even in our tough periods this year we have still been competitive for the most part."
Kulusevski scored his seventh and eighth Premier League goals of the season (36 outings), more than he managed in his first two league campaigns with Tottenham combined (seven across 48 games).
Only in the 2019-20 season with Parma has the Sweden winger scored more times in a league season (10 in Serie A), and Postecoglou hailed Kulusevski's returns.
He added: "I thought Deki was good. He's worked awfully hard this year without a lot of reward in the front third.
"We thought playing him through middle today would help us with his mobility and ability to run in behind. He did well.
"He always works hard but it's that sort of final third where we need him to get rewards and he got them today so he did well."
Walker: Man City driven on by creating history
Kyle Walker believes Manchester City were spurred on by creating history to a fourth straight Premier League title.
A Phil Foden double and a Rodri strike saw City beat West Ham 3-1 on Sunday as they claimed a fourth consecutive Premier League crown, finishing two points above Arsenal.
In doing so, City became the first team ever to win England's top division four times in a row, and Walker feels that was one of the key motivations behind the team finishing top of the Premier League pile yet again.
When asked if creating history had driven him and his team-mates on, Walker told Sky Sports: "I think so, I think so. We went out of the Champions League, got into the FA Cup final, but to do this, make it four in a row, it made it something special.
"It has been spoken about all year what we can achieve and the history we can make. But it is about the finer details. It was down to just one game and that game was West Ham United. We get past that then we make history, but more importantly we claim the Premier League again.
"It is a very, very tough league to win. I looked at the Italian league, German league, Spanish league, the winners are 10, 15 points clear. Fair play to Arsenal and Liverpool for what they have done throughout the season, making sure they push us right to the limit."
Walker turns 34 later this month but has shown little signs of slowing down, playing an integral role again this season on his way to a sixth Premier League title of his decorated career.
Walker still feels he is capable of playing at the top level, saying: "I feel young. I don't know if that is a good thing or a bad thing. I feel young, I feel great, I still have my pace.
"I come to training every day wanting to learn. Once that goes then it is probably time to pack up, but this group of lads keeps you on your toes. They keep on you to keep improving every day."
Walker has been City's captain this season, making his 300th appearance for the club in the title-securing win over West Ham.
The defender was keen to emphasise that it has been a collective effort this term, though, explaining: "I am the man at the front and I wear the armband, but I don't put myself above anyone else. We are a team.
"There are four captains including myself, and we all pull our weight. I am just the man they've picked to wear the armband which I am very grateful for. To be able to lift the trophy in this scenario, the four in a row, it is a dream come true."
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