Luis Diaz started for Liverpool hours after his kidnapped father was released but lost 3-2 at Toulouse on Thursday as West Ham secured European football in 2024 and Leverkusen progress.
The stunning upset in France came courtesy of goals from Aron Donnum, Thijs Dallinga and Frank Magri as Liverpool sank to their first defeat in the Europa League this season.
However, the game was not without controversy with VAR stepping in to rule out an equalizer deep into injury time from Jarell Quansah.
“He deserved to lose because he won almost all the decisive challenges, the battles,” Liverpool manager Jurgen Klopp said as his side missed the chance to book their place in the knockout stages.
Toulouse now sit on seven points, two behind the Premier League side and three ahead of third-placed St Gilloise in Group E.
With 36 minutes gone, Donnum raced past Kostas Tsimikas and stole possession before slotting home through a deflection to give Toulouse the lead at the break.
The surging hosts got a second when Dallinga took a touch in the box and slotted past Caoimhin Kelleher on 58 minutes.
A Cristian Casseres own goal in the 73rd minute gave Liverpool a lifeline but the hosts, pressed by a lively home crowd, hit back immediately.
Three minutes later, Kelleher couldn’t hold on to a well-struck cross and Magri was on hand to restore Toulouse’s two-goal deficit.
Diogo Jota, on for Diaz, scored a second for Liverpool in the 89th minute.
The home side were able to see the game out to claim a valuable treble, but not before an equalizer seven minutes into injury time from Quansah was ruled out following video review for an assessed handball much earlier in the build-up.
Last year’s Europa Conference League winners West Ham demolished Olympiakos with Lucas Paqueta’s 73rd minute goal the difference between the two sides.
“I’m really happy we got the result. We didn’t play as well as we would have liked, but Olympiacos are a decent team,” West Ham manager David Moyes told TNT Sports.
The win takes them top of Group A and with nine points they are assured of either the Europa League or the Europa Conference League in the new year.
Villarreal beat Maccabi Haifa 2-0 in Larnaca, Cyprus with the game altered by the Israel-Hamas conflict.
Rennes beat Greece’s Panathinaikos 3-1, while France’s Marseille climbed to the top of Group B with a 2-0 win at AEK Athens.
In Group B, Brighton took a big step towards booking their place in the knockout stages with a comfortable 2-0 win at Ajax.
Goals either side of the break from Ansu Fati and Simon Adingra gave the Seagulls a famous win at the home of European rights.
The Premier League side now have seven points and are three clear of third-placed AEK.
Rangers claimed a crucial treble over Sparta Prague with a 2-1 home win thanks to Danilo and Todd Cantwell.
Bundesliga leaders Bayer Leverkusen completed qualification for the knockout stages with a 1-0 win in Baku against Group H rivals Qarabag.
A Victor Boniface penalty in the fourth minute of second-half injury time was enough to give Xabi Alonso’s side a fourth win in four.
Along with Atalanta’s 1-0 win over Sturm Graz, Leverkusen have booked their place in the next phase of the competition, ensuring they will at least reach the knockout play-offs.
The second biggest surprise of the night came in Prague when Slavia Prague demolished Jose Mourinho’s Roma 2-0 to leapfrog the Italians into top spot in Group G.
“I can’t explain this. I don’t know myself,” Mourinho said. “I’ll be honest — Slavia deserved to win and Roma deserved to lose.”
Strikes from Vaclav Jurecka in the 50th minute and Lukas Masopust 16 minutes from time handed Roma their first defeat of the season and sent Slavia top of the table with nine points, level with the visitors.
In the other group game, Swiss side Servette beat Sheriff Tiraspol 2-1 thanks to a 92nd-minute penalty from Chris Bedia.
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