Simon Kjaer's last-gasp equaliser gave AC Milan a dramatic 1-1 draw at Manchester United on Thursday, handing the Italian giants a great chance of reaching the Europa League quarter-finals.
Kjaer netted with a bullet header in the final seconds of stoppage time of the last 16, first leg encounter at Old Trafford, levelling the scores after Amad Diallo had opened in the 50th minute with his first United goal.
In a sign of the drop in standards at Old Trafford and the San Siro, the first meeting between two of the world's most historic teams since 2010 was their first outside the Champions League knockout stages.
Milan called the shots early on and had two goals disallowed, Rafael Leao's effort ruled offside and Franck Kessie's powerful 11th-minute finish chalked off after a VAR review showed the ball had glanced off the midfielder's arm before his shot.
Diallo's introduction at half-time proved an inspired move from United coach Ole Gunnar Solskjaer as he soon broke the deadlock.
Bruno Fernandes unfurled a delightful long pass towards the 18-year-old Diallo, who made an incisive run behind the Milan defence and looped a clever backwards header over Gianluigi Donnarumma.
But United failed to build on that lead and Milan's intelligent play was rewarded with just seconds left when Kjaer powered his header past Dean Henderson from a corner.
Rangers are well placed to make the quarter-finals after a 1-1 draw away to Sparta Prague.
Filip Helander's close-range finish in the first half left Steve Gerrard's Rangers in the hunt for a European title with the draw in Prague, days after winning their first Scottish League title in 10 years.
Nicolae Stanciu had rewarded the hosts for their stronger start with the opening strike in the seventh minute that fizzed passed Rangers goalkeeper Allan McGregor before the Scotsman even knew it had been hit.
However, Rangers levelled against the run of play nine minutes before the break when Helander pounced to tap home the easiest of opportunities amid chaos in the Sparta box following Borna Barisic's free-kick.
Ondrej Kolar made a super save to stop the away side from getting a second away goal when he stretched out a hand to push away Ryan Kent's mishit shot that nonetheless was looping towards the top corner.
It was McGregor who pulled off the save of the match however when he somehow saved and held on to Lukas Masopust's thumping header, which looked destined for the bottom corner.
Four-time European champions Ajax are almost guaranteed a place in the last eight after thumping Young Boys 3-0 in Amsterdam through goals from Davy Klaassen, Dusan Tadic and Brian Brobbey.
Klaassen put the Eredivisie leaders ahead in the 62nd minute by firing home after the ball bobbled to him following a quick exchange of passes with Tadic.
Tadic made Ajax overwhelming favourites to qualify with eight minutes left by coolly slotting home the second following another fortunate ricochet in the box.
Their passage was then more or less secured in stoppage time of a dominant performance, 19-year-old Brobbey tucking home from a tight angle after brilliantly collecting Ryan Gravenberch's quick through ball.
Villarreal also look good to make the quarters thanks to a 2-0 win at Dynamo Kiev.
A Pau Torres tap-in on the half-hour mark and Raul Albiol's strike six minutes after the break gave La Liga outfit Villarreal a comfortable lead going into next week's second leg in Spain.