Gabriel Martinelli missed from the spot as Arsenal lost 5-3 in a penalty shootout to Sporting in the Europa League last-16.
Manchester United cruised into the Europa League quarter-finals with a 5-1 aggregate win over Real Betis after a 1-0 victory in Spain.
Manchester United bounced back from Sunday's trouncing at Liverpool with Antony's stunner helping them cement a 4-1 first-leg Europa League last-16 lead over Real Betis.
Arsenal fought back to earn a 2-2 draw in an action-packed and error-filled Europa League last-16 first leg at Sporting.
Erik ten Hag admitted Manchester United "need options" up front after they failed to score enough goals against Real Sociedad to avoid a Europa League play-off tie.
Kieran Tierney's sublime first-half strike was enough to ensure Arsenal held onto top spot in Europa League Group A as FC Zurich were beaten 1-0 at the Emirates Stadium.
Alejandro Garnacho's first senior goal gave Man Utd a 1-0 win over Real Sociedad in Spain, but it was not enough for Erik ten Hag's side to top their Europa League group.
Man Utd qualified for the Europa League knockout stage as Cristiano Ronaldo marked his return to the side with a goal in a 3-0 win over Sheriff Tiraspol.
Luuk de Jong scored one & assisted another in a second-half cameo as PSV beat Arsenal 2-0, with the Gunners missing the chance to seal top spot in Europa League Group A.
Rangers suffered a narrow defeat to RB Leipzig in the first leg of their Europa League semi-final after a moment of brilliance from Angelino.
West Ham's chances of reaching a first European final for 46 years hang in the balance after they lost 2-1 to Frankfurt in their Europa League semi-final first leg.
A West Ham side including six homegrown players were narrowly beaten 1-0 by Dinamo Zagreb in their dead rubber final Europa League group game at the London Stadium.
Celtic lost strikers Kyogo Furuhashi and Albian Ajeti to hamstring problems as they rounded off their Europa League campaign with a 3-2 victory over Real Betis.
Leicester were eliminated from the Europa League after suffering an agonising 3-2 defeat to Napoli at the Stadio Diego Armando Maradona.
Rangers remain unbeaten under Giovanni van Bronckhorst after earning a 1-1 draw with Lyon to cement their place as runners-up in Group A.
West Ham closed in on the Europa League knockout stages as two goals in two minutes helped them to a 3-0 home win over Genk.
Borussia Dortmund's Jadon Sancho and Erling Haaland scored two goals apiece to crush RB Leipzig 4-1 and lift the German Cup at the Olympiastadion in Berlin.
Everton's European chase stuttered as they played out a poor 0-0 draw with Aston Villa at Villa Park and missed the chance to go sixth in the Premier League table.
Olivier Giroud gave Frank Lampard a reminder of his qualities with four goals that helped Chelsea confirm top spot in Group E with a 4-0 win at Sevilla.
West Brom owed their first win of the season to Conor Gallagher's fine strike in a 1-0 victory over wasteful Sheffield United, who stay bottom.