Sevilla crashed out of the Champions League on Wednesday, throwing away a two-goal lead in a 3-2 defeat by PSV Eindhoven.
Leading through goals from Sergio Ramos and Youssef En-Nesyri, Sevilla winger Lucas Ocampos was sent off for two bookings in four minutes and it opened the door for PSV's fightback.
The Dutch side silenced Sevilla's Ramon Sanchez-Pizjuan stadium as Ismael Saibari volleyed home for the visitors and then Nemanja Gudelj bundled into his own net.
United States forward Ricardo Pepi headed home the winner in stoppage time to end Sevilla's hopes of reaching the last 16.
PSV's win leaves them second, a point behind Group B leaders Arsenal, who face Lens, third, later Wednesday.
Seven-time Europa League winners Sevilla could still qualify for that competition, if Arsenal beat Lens and then Sevilla do the same in the final group match.
Sevilla have not won a single game under coach Diego Alonso in the Champions League or La Liga -- they have suffered four defeats and four draws since he took over in October.
The night had begun so positively for Sevilla.
Ramos started his 141st Champions League match, equalling Manchester United legend Ryan Giggs in ninth in the all-time list.
The veteran centre-back, 37, celebrated with a goal to break the deadlock, converting from close range after Ivan Rakitic's free-kick found its way through to him at the back post.
It was Ramos's first goal for Sevilla after rejoining his former club from Paris Saint-Germain this summer.
The lead was just reward for a strong start by Sevilla and they continued to dominate the match, with Djibril Sow netting a second, but it was disallowed for a handball earlier in the move.
En-Nesyri headed against the bar before half-time as Alonso's side played with a confidence they have not displayed in recent weeks.
The Moroccan striker netted Sevilla's second early in the second half with a neat flicked finish over goalkeeper Walter Benitez after running on to Marcos Acuna's long ball.
Sevilla were cruising, but winger Ocampos was sent off for two bookings in four minutes, the second for crashing into Yorbe Vertessen, giving PSV hope.
Two minutes later Saibari pulled them back into the game with a spectacular volley from Sergino Dest's cross, putting the hosts against the ropes.
Vertessen forced the equaliser with his cross turned clumsily into his own net by Gudelj, leaving the hosts clinging on for a point as the clock ticked down.
They could not even claim that, with 20-year-old striker Pepi's header from Vertessen's cross sealing their fate.
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