Ten-man Tottenham Hotspur crashed out of the Europa League in the round of 32 after losing 3-2 on aggregate following Thursday’s 2-2 second-leg draw against Belgian club Gent at Wembley.
Harry Kane’s own goal and Dele Alli’s first-half red card were too much to overcome as Mauricio Pochettino’s men failed to reach the quarterfinals of the competition for a fourth consecutive campaign.
However Christian Eriksen gave Tottenham early hope in the 10th minute, levelling the tie with a calm finish past goalkeeper Lovre Kalinic after collecting a speculative long ball behind the Gent defence.
Gent complicated things 10 minutes later, securing a crucial away goal with the help of Kane, who, from a Gent corner kick, mistakenly headed past Tottenham keeper Hugo Lloris.
And Alli added to Spurs’ misery in the 39th minute when he was given a red card for a studs-up kick of Brecht Dejaegere while battling for the ball near the sideline.
Victor Wanyama struck a sweet shot from just inside the box on the hour mark as Tottenham piled on the pressure — his lifted shot beating a diving Kalinic to the far corner.
But Gent finished off the tie in the 82nd minute through second-half substitute Jeremy Perbet, whose deflected shot trickled past Lloris to hand the eighth-placed Belgian side a memorable night at historic at the historic stadium.
Athletic Bilbao also were eliminated following a 2-0 defeat at APOEL, falling to the Cypriot side 4-3 on aggregate.
Pieros Sotiriou opened the scoring in the first minute of the second half and Giannis Gianniotas converted a penalty soon after to complete the comeback.
And though Sotiriou was sent off for a second yellow card in the 65th minute, the favoured Spanish club could not find the two goals they needed to advance before their substitute Ander Iturraspe was also dismissed late on.
With a comfortable lead from their first-leg win, Roma cruised into the round of 16 past Villarreal 4-1 on aggregate despite losing the second leg 1-0 at home.
Rafael Santos Borre took advantage of a loose ball in the box to score for Villarreal on 15 minutes, but the deficit was too great for the Spanish club.
However, they will have to open the next round without Antonio Rudiger after the defender saw a red card in the 81st minute.
Meanwhile, Celta Vigo — the last Spanish side remaining — needed a stoppage-time penalty to reach extra time at Shakhtar Donetsk.
Lars Stindl converted a hat trick to rally Borussia Monchengladbach past Fiorentina with a 4-2 win in Italy.
Fiorentina added to their 1-0 first-leg win with first-half goals from Nikola Kalinic and Borja Valero, the latter on hand to clean up from Jannik Vestergaard’s comical failed clearance.
But Stindl started the comeback just before the break, converting a penalty after Maximiliano Olivera fould Patrick Herrmann in the box.
Stindly then scored two minutes into the second half following a corner and completed his treble from a set piece on 55 minutes.
That put Gladbach ahead on away goals, and Andreas Christensen added a fourth goal five minutes later to secure the result.
Isaac Kiese Thelin scored in the 90th minute for Anderlecht to secure a dramatic result against Zenit St Petersburg, with the Belgian club advancing on away goals.
A brace from Giuliano allowed Zenit to overcome a first-leg 2-0 defeat to lead 3-2 on aggregate, but Thelin’s late header silenced the home crowd as the second leg finished 3-1 and the tie ended 3-3 on aggregate.
Giuliano showed good control in the box to reduce the hosts’ deficit in the 24th minute, before Artem Dzyuba brought the tie level with a low shot from 12 yards on 72 minutes.
And the Brazilian was again on target six minutes later, turning in Dzyuba’s cross and taking his Europa League tally to eight goals in as many games, making him joint-top scorer with Roma’s Edin Dzeko.
But Thelin’s late goal meant Zenit’s comeback was all for naught.
Another Russian club had no such trouble advancing as FC Rostov are through after a 1-1 draw at Sparta Prague to complete a 5-0 aggregate romp.
Dmitry Poloz’s 13th-minute goal ended any hopes of a comeback for Sparta, who had Costa Nhamoinesu sent off in the second half before Vyacheslav Karavaev scored a consolation goal.
A hat trick from Nabil Fekir was more than enough for Lyon, who completed a 11-2 aggregate thrashing of AZ Alkmaar with a 7-1 home win.
Fekir ran in on goal to open the scoring after five minutes and — after Lyon’s Maxwel Cornet and AZ’s Levi Garcia traded goals — added a second from a deflected shot following a corner before the half-hour mark.
Sergi Dardar soon added Lyon’s fourth on the night, and Fekir tapped home a cross in the second half to complete his hat trick before Houssem Aouar and Mouctar Diakhaby also got in on the fun late on.
Despite a goalless draw in their home leg, Olympiakos advanced with a 3-0 win away to Osmanlispor in Ankara, Turkey.
The Greek giants broke through two minutes after halt-time through Karim Ansarifard’s goal following a corner kick. Tarik Elyounoussi’s header on 70 minutes doubled the visitors’ advantage before Ansarifard added his second with four minutes to play.
With Fenerbahce also going out of the competition on Wednesday, Besiktas are the only Turkish side remaining after securing a 5-2 aggregate triumph after a 2-1 win with Hapoel Be’er Sheva.
Vincent Aboubakar scored from a hard shot in the box on 17 minutes to give Besiktas a three-goal aggregate lead, and though Anthony Nwakaeme got a goal back in the second half, it was too much for the Israeli side to overcome, and Cenk Tosun’s late goal secured the second-leg win.
Nick Viergever turned in a rebound early in the second half for the only goal as Dutch giants Ajax advanced past Poland’s Legia Warsaw 1-0 after a goalless first leg.
Racing Genk got the result they needed to advance as Alejandro Pozuelo found the breakthrough in the 67th minute to secure a 1-0 win over Astra Giurgiu, the Belgian side going through 3-2 on aggregate.
FC Copenhagen held on for a goalless draw at home against Ludogorets Razgrad to advance 2-1 on aggregate.