Newcastle United's first Champions League journey in 21 years ended at the first hurdle as AC Milan came from behind to prevail 2-1 in their final Group F encounter at St James' Park.
In order to sneak into second place and prolong their top-tier European adventure, Eddie Howe's side had to overcome the Italian giants and pray for Borussia Dortmund to avoid defeat against Paris Saint-Germain, who began the final matchday two points better off.
Dortmund did their bit by holding PSG to a 1-1 draw, and a Joelinton rocket had the Magpies on course for a coveted last-16 place, but second-half responses from Christian Pulisic and Samuel Chukwueze dumped Howe's crestfallen troops out of Europe entirely.
While Milan received a major boost with Rafael Leao's return to fitness, Newcastle boss Howe was finally able to make an alteration to his overworked starting XI, giving Callum Wilson the nod to lead the line ahead of Alexander Isak.
The Magpies' fatigue was evident against Everton and Tottenham Hotspur, but Howe's men took the game to Milan as soon as the first whistle blew inside the ear-piercing St James' Park cauldron.
In an opening period inundated with fouls and stoppages, Kieran Trippier fizzed a free kick just over the crossbar with six minutes on the board, before Fikayo Tomori produced an outrageous tackle to deny Miguel Almiron a one-yard tap-in in the 20th minute.
A rare foray forward from the Rossoneri in the 24th minute ended with the fit-again Leao curling a promising chance wide of Martin Dubravka's goal, but Newcastle continued to bombard their visitors' backline and were rewarded in the 33rd minute.
The lively Anthony Gordon drove forward in a pocket of space before laying off 17-year-old Lewis Miley, who in turn teed up Joelinton just inside the box, and the Brazilian took one touch before unleashing an unstoppable effort into the top corner.
As news filtered through that Borussia Dortmund had taken the lead against PSG, cheers erupted inside St James' Park while Wilson sent a tame shot into Maignan's arms in the 51st minute, although the hosts' fortunes soon took a turn for the worse.
Only a few minutes after PSG equalised against Dortmund, Leao beat the offside trap and delivered a sublime cross into the box, where Tomori mishit his volley before Olivier Giroud smartly teed up Pulisic to slot home from close range.
Needing to up the ante, Newcastle forced Maignan into a spectacular save in the 69th minute, as the Frenchman tipped a Bruno Guimaraes curler from inside the D onto the crossbar, but Howe's side were almost caught cold in the 79th.
A poor touch from Tino Livramento allowed Luka Jovic to set Leao on his way, and the Portugal international attempted to beat Dubravka at his near post, but his low strike cannoned off the frame of the goal to the delight - and relief - of the St James' Park faithful.
However, Jovic was one of three substitutes to combine for a Rossoneri sucker punch in the 84th minute, as the Serbian and Noah Okafor burst through a disjointed Newcastle outfit on the counter-attack, and the latter set up Chukwueze to curl a sublime finish across Dubravka's futile dive.
As Newcastle sent every man forward in a frenetic injury-time period, Milan wasted two glorious chances to inflict more misery on the Magpies, as Theo Hernandez missed an open goal from inside his own half after Dubravka went up for a corner, before Tomori also struck the post after a last-minute counter.
Those wasted openings came too late for Newcastle to capitalise, though, as Howe's team finished bottom of Group F to bow out of continental football, while Milan will continue their European adventure in the Europa League as Dortmund and PSG advance to the last 16 of the Champions League.
One of two English teams to finish last in their group alongside Manchester United, Newcastle seek to bounce back in Saturday's Premier League clash with Fulham, while Stefano Pioli's Milan meet near neighbours Monza in Sunday morning's Serie A tie.
