Arsenal will be in the Europa League quarter-finals but their North London rivals Tottenham will not after an embarrassing night for Jose Mourinho’s men.
Both sides had won their first leg ties against Olympiacos and Dinamo Zagreb respectively, only to lose in their second leg matches.
However, while Mikel Arteta’s men lost 1-0 to the Greeks, a result which ensured a 3-2 aggregate success, Spurs came unstuck in the Croatian capital.
Leading 2-0 from their first encounter, they fell to a 3-0 defeat after extra time, with Mislav Orsic scoring a sensational hat-trick.
Unsurprisingly, it left Mourinho furious as his hopes of continuing his 100 percent record in European football’s secondary competition went up in smoke.
Manchester United joined Arsenal in the final eight, after securing victory in Milan.
Spurs weren’t the only British side to fall however, as Steve Gerrard’s Rangers fell to Leicester City’s conquerors, Slavia Prague.
The Scottish champions had two men sent off as they lost 2-0 at Ibrox, ensuring a 3-1 aggregate defeat.
Elsewhere, Ajax made light work of Young Boys in Switzerland to book their last eight place with a 5-0 aggregate win – keeping alive hopes of a 2017 Final repeat against United – while Villarreal eased past Dynamo Kyiv.
The Yellow Submarines aren’t the only Spanish side through, as Granada held off Molde to win 3-2 on aggregate.
Roma are also into the last eight, winning 2-1 against Shakhtar Donetsk after a 3-0 first leg success.
Europa League quarter-final qualifiers
- Dinamo Zagreb
- Manchester United
- Slavia Prague