One of the biggest nights St James' Park had ever seen ended in heartbreak for Newcastle.
Joelinton put Newcastle ahead with a stunning goal on the half-hour mark. Christian Pulisic's equaliser was followed by Mike Maignan pulling off a stunning save to deny Bruno Guimares whilst the game was all square proved pivotal, as Samuel Chukuweze's late goal sent Milan to the Europa League and consigned Newcastle to the end of their latest European chapter.
Before kick-off, the usual trials and tribulations with the final matchweek in Group Stage football were in full effect. Both Newcastle and Milan needed wins to keep their hopes of playing European football alive in 2024.
The two other sides in Group F, Borussia Dortmund and Paris Saint Germain had contrasting outcomes to bear in mind too. Dortmund only needed to avoid defeat to finish top of the group, with PSG needing to win and rely on the result on Tyneside to learn their fate.
Newcastle boss Eddie Howe named just one change to the side that was soundly beaten at Tottenham Hotspur Stadium on Sunday, with Callum Wilson coming in for Alexander Isak, who dropped to the bench.
Of The Toons' notable long-term absentees, only Dan Burn returned to matchday 18, with Sandro Tonali, Sven Botman, Nick Pope, Matt Targett, Joe Willock, Jacob Murphy, Elliot Anderson and Harvey Barnes all still absent long-term.
AC Milan also made just one change from their team that lost 3-2 to Atlanta at the weekend, with Rafael Leao having fully recovered from a hamstring injury to return to the squad.
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Story of the Match:
The players emerged out of the tunnel at St James' Park to a cauldron of noise and a sea of black and white flags. A banner on the Gallowgate End read, "It's not beyond our wildest dreams, because we have had wild dreams." - The stage was set and then some.
The first chance did fall to the hosts, with the Paraguayan, Miguel Almiron whipping a dangerous left footed cross in, which Fikayo Tomori sliced up into the air but Milan keeper, Mike Maignan gratefully clutched the ball to his chest.
The Geordies had another chance with their first clear shot at goal; Anthony Gordon was brought down about thirty yards from goal, with Kieran Trippier sending a dipping free kick just over the crossbar.
Newcastle were aggressive in their start during the first quarter of the game, averaging 63% possession within the first 15 minutes and only denied a route to goal by two superb last-ditch challenges, one from Ruben Loftus-Cheek, and one from Theo Hernandez.
On the 19-minute mark, Newcastle somehow didn't make their early dominance count. Joelinton made a burst through midfield and looked to pull the ball across for Almiron, who couldn't have been more than about two yards out, but former Chelsea man Tomori somehow managed to hook a leg around and send the ball behind whilst all of St James' Park probably thought Newcastle had opened the scoring.
Milan then hit back with a warning shot for Newcastle when they broke down the left wing, with Rafael Leao finding himself in space on his right foot in the box, but the finish lacked any conviction and flew harmlessly wide of Martin Dubravka's goal.
Joelinton again was the man picking up all sorts of pockets and areas of space for The Toon, this time whipping a ball onto the head of Almiron, whose header was well held by Maignan in the AC Milan goal.
With just over half an hour gone, the Brazilian Number 7 smashed the breakthrough past Maignan. Anthony Gordon picked the ball up and drove infield to find 17 year old, Lewis Miley, who cut the ball back to Joelinton, who flicked the ball up and smashed an unstoppable right-footed effort into the top corner to take the roof off of St James' Park.
The Brazilian so nearly had a second two minutes before half time too, with a stunning Kieran Trippier delivery being met by the head of Joelinton, but the ball bounced off the Newcastle man, rather than being directed towards goal.
Rather bizarrely, AC Milan goalkeeper Mike Maignan was the first name in the referee's book for his reaction towards the referee, Danny Makkiele, when a foul was given in his favour in the last action of the half.
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Second Half:
With neither team making a change at the break, the game got back underway for a tense second 45 on Tyneside, with Callum Wilson having a chance within the first thirty seconds of the restart, bending an effort into the arms of Maignan in the Milan goal.
There was a cheer almost as loud for the Newcastle goal on the 50th minute, when the news filtered through that Karim Adeyemi had put Borussia Dortmund 1-0 up against PSG in Germany, to effectively put Paris at risk of a humiliating exit into the Europa League.
This night was about Newcastle however and young Lewis Miley in particular, putting in a stellar performance to people years and years his senior. A few lids went back on Geordie emotions, however, as news of a PSG equaliser in Germany stuck the group back in the melting pot.
Newcastle then tried a quick, rehearsed corner routine which nearly came to the fore, Bruno Guimares and Anthony Gordon combined well to fizz the ball to Almiron on the edge, but the winger couldn't connect with the effort and the ball fizzled away.
In the blink of an eye however, the Newcastle lead was gone, as Leao floated into the middle and his mishit cross bobbled about, and fell to Oliver Giroud who squared the ball for Christian Pulisic who had a tap in to bring the game level and because of the PSG equaliser, move the Premier League side to third in the group on the hour mark.
Eddie Howe made two changes shortly after the goal, bringing on the returning Dan Burn for Kieran Trippier, and Alexander Isak coming on in place of Anthony Gordon.
With the spaces starting to open up, Guimares and Joelinton combined to feed the ball out to Isak whose curling effort didn't dip enough in time to trouble the French keeper, Maignan in the Milan goal.
Isak once again took on Calabria down the left and pinned the ball back for Guimares who took a touch and bent a stunning effort towards goal which was superbly tipped onto the crossbar by Mike Maignan. The Brazilian midfielder then fed Miguel Almiron who displayed fantastic footwork to pull the ball back, but it just evaded Callum Wilson who was free and waiting in the middle.
Howe's next roll of the dice was to bring on Sean Longstaff for teenager Lewis Miley who departed the pitch to a standing ovation after another composed and assured performance.
AC Milan then made their first changes, with Ruben Loftus Cheek and Christian Pulisic being replaced by Tomasso Pobega and Luka Jovic to offer something different in the Milan attack.
With the tie sitting on a knife edge, 12 minutes from time, Rafael Leao burst through on goal, looked to give Martin Dubravka the eyes and roll the ball into the bottom left corner, but the ball cannoned back off the post, much to the relief of most inside St James' Park.
With both sides needing the win, Milan threw on Noah Okafor and Samuel Chukwueze in place of Oliver Giroud and Yunnus Musah,
The change paid dividends almost instantly, as Fabian Schar made a forward burst which left his defence exposed, allowing AC Milan to break downfield and see fellow sub, Okafor, roll the ball into the path of Chukwueze, for his first touch to dump Newcastle out of Europe all together.
Another substitute, Jovic, had a chance to kill the game after being found on the edge of the box by Leao, but a brilliant block from Dan Burn just about kept Newcastle in the contest, and in Europe.
As four added minutes went up on the board, a huge roar of encouragement by the Toon faithful rang out, knowing a goal would keep them in European competition in the latter part of the season.
Martin Dubravka was sent forward for a Newcastle corner in added time, which Milan broke from and Theo Hernandez picked the worse of two options, with his slow effort bobbling wide of an empty goal.
Milan had yet another chance to seal it on the break, with Okafor and Jovic's movement combining to free up Tomori, whose effort bounced back off the post, with that being the final action of the game.
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Player of the Match: Joelinton
Despite being on the losing side, Joelinton embodied everything good about Newcastle tonight.
His goal in particular, flicking it up and pinging a stunning, stirring effort into the top left corner, leaving Maignan rooted to his spot, at the time, sparked serious delirium amongst the Newcastle faithful.
He constantly picked up brilliant little pockets of space and was always eager to get on the ball and cause AC Milan issues, which he did throughout. Even at 2-1 down in injury time, he was the man driving Newcastle forward and urging the fans on. A complete midfielder's performance from the Geordie's Number 7.