Arsenal's hopes for a European title ended when the Premier League leader was eliminated from the Europa League by Sporting Lisbon in a penalty shootout.
Lisbon reached the quarterfinals by prevailing 5-3 in the shootout at the Emirates Stadium on Thursday after a 1-1 draw in regulation in the second leg of their round-of-16 encounter. The first leg ended 2-2.
Gabriel Martinelli failed to convert from the spot for Arsenal.
"It's a huge blow," Arsenal manager Mikel Arteta told BT Sport.
"There were moments, especially during the first 75 minutes, when we weren't at our level and gave every ball away." Meanwhile, Manchester United cruised into the quarterfinals after a 1-0 victory at Real Betis.
Arsenal dominated the extra time with playmaker Martin Ødegaard coming on as a substitute but Sporting goalkeeper Antonia Adán made some stunning saves to force the shootout.
Manuel Ugarte was sent off two minutes before the end of extra time after picking his second yellow card.
Granit Xhaka gave Arsenal a first-half lead on a rebound to complete a flowing move by the hosts. Martinelli had his effort on goal blocked by Adán but the ball came into Xhaka's path for the Arsenal captain to curl it into the net from inside the area.
Pedro Gonçalves leveled the score on the hour to spark the visitors' attack and force extra time.
Rashford on target as United advances
In Seville, Marcus Rashford produced a clinical finish in the 56th minute, finding the bottom corner of the net with a low drive from outside the area to help United advance on a 5-1 aggregate score in the second-tier European competition.
Rashford's 27th goal of the season came after the striker wasted several decent chances to put the visitors ahead at the Benito Villamarin stadium in Seville.
"Betis are a really good team, we saw that against Real Madrid and Barcelona, but we beat them twice so I think we performed really well," manager Erik ten Hag told BT Sport.
"Second half, we were much better on the ball, keeping it in their half and then you create chances.” United won 4-1 in the first leg at Old Trafford last week.
Following a 0-0 draw against Southampton in the Premier League on Sunday, Ten Hag made four changes in his starting lineup with right winger Facundo Pellistri getting his first start for the club.
United won the Europa League in 2017.
Feyenoord’s rout
Feyenoord overwhelmed Shakhtar Donetsk 7-1 in Rotterdam to advance 8-2 on aggregate.
Shakhtar was the last Ukrainian team in European competitions. The teams drew 1-1 in the first leg played in Poland due to Russia's invasion of Ukraine.
Orkun Kökçü scored twice, the second one from the spot, in the first half and Oussama Idrissi struck twice in the second to lead the rout.
Santiago Gimenez, Alireza Jahanbakhsh and Danilo Pereira also had one each for the Dutch club before Kevin Kelsy got a consolation one for the visitors.
Betis' crosstown rival Sevilla was more successful despite losing 1-0 at Fenerbahçe. Sevilla, the six-time Europa League champion, advanced 2-1 on aggregate. Enner Valenicia scored the winner four minutes before the break for Fenerbahçe.
Juventus beat 10-man Freiburg 2-0 to advance 3-0 on aggregate.
Dušan Vlahovic converted from the penalty spot and substitute Federico Chiesa doubled the advantage in stoppage time for the Italian powerhouse.
Leverkusen beat Ferencváros 2-0 to advance. Roma progressed despite a 0-0 draw at Real Sociedad after a 2-0 win in the first leg.
Belgium's Union Saint-Gilloise moved into the quarterfinals with a 3-0 win over 10-man Union Berlin in Brussels after a 3-3 draw last week.
Europa Conference League
West Ham outclassed AEK Larnaca 4-0 in London. Jarrod Bowen struck twice in two minutes early in the second half to extend West Ham's lead to 3-0 after Gianluca Scamacca's opening goal in the first half. Substitute Divin Mubama added the fourth to keep a perfect record in Europe this season.
Europa League semifinalists last season, a 6-0 aggregate victory sent the Hammers to the quarterfinals of the third-tier European competition.
Lazio was eliminated by Dutch club AZ Alkmaar after losing 2-1 in both legs.
Fiorentina rallied to beat Turkey's Sivasspor 4-1 to progress 5-1 on aggregate. Sivasspor finished the home game with 10 after captain Hakan Arslan picked a red card.
Anderlecht had a 1-0 win at Real Sociedad for a 2-1 advancement while Nice was in command for a 4-1 aggregate victory after winning 3-1 at home over Sheriff.
Sweden's Djurgarden lost 3-0 to Polish club Lech Poznan for a 5-0 aggregate elimination. Basel won a penalty shootout 4-1 after the match against Slovan in Bratislava went to extra time after the two teams were 4-4 on aggregate.
On Wednesday, Gent advanced by beating Turkish club Istanbul Basaksehir 4-1.
