Nine-man FC Zenit St. Petersburg survived a late Villarreal CF onslaught to reach the Round of 16 on away goals, despite losing 2-1.
Pavel Pogrebnyak, Zenit's match-winner in the first leg, seemed to have sealed the outcome, with his first-half strike leaving the Primera División side needing three goals to progress. However a 47th minute red card for Roman Shirokov, a Guille Franco goal 15 minutes from time, Radek Širl's dismissal seven minutes later, and Jon Dahl Tomasson's added-time effort ensured Zenit an uncomfortable end to the evening.
Following their 1-0 defeat in Russia, Manuel Pellegrini's side set out in search of an early goal to restore parity, and almost did so when Robert Pires' cross evaded Tomasson. And Villarreal went even closer to levelling the tie on 14 minutes, when Marcos Senna's curling free-kick was grasped at the far post by a grateful Vyacheslav Malafeev.
Dick Advocaat's team gradually found their rhythm and won a series of corners midway through the first half. Villarreal's defence was also showing signs of nerves and it was no surprise when the Russian champions took the lead from a set piece after 31 minutes – Pogrebnyak punishing Diego López's flapped clearance to head into an empty net.
Needing three goals to progress, the hosts were boosted just after the interval when Shirokov was sent off for a second bookable offence. Villarreal should have levelled two minutes later, but Giuseppe Rossi poked the ball just wide from Pires' cross. Tomasson was also off target 56-minute header as the home side continued to press. But half-time substitute Guille Franco gave Pellegrini's men hope on 75 minutes when he headed home an equaliser.
The Spanish side piled forward, but a second goal was proving elusive until the visitors were reduced to nine men when Širl was also sent off after seeing yellow twice. Tomasson scored a second to set up a grandstand finale, but the Russians held on through five minutes of added time to book a Round of 16 encounter with Olympique de Marseille.