Club Brugge KV will take a narrow advantage to Spain after Dorge Kouemaha's goal helped them win 1-0 against ten-man Valencia CF in their round of 32 first leg.
Both sides squandered good chances before David Silva's red card after half-time was quickly followed by Kouemaha's 56th-minute opener. It was Club Brugge's first post-Christmas win in Europe for six seasons and ended Valencia's 18-match unbeaten run in continental competition.
In a lively opening, the hosts were first to threaten when Joseph Akpala teed up strike partner Kouemaha, who was only denied by a sprawling Miguel Ángel Moyá. The visitors' David Villa provided a prompt response by serving notice of his threat with a fierce strike that home goalkeeper Stijn Stijnen was forced to beat away.
From the resulting corner, Rubén Baraja found himself unmarked but smashed his effort straight at Stijnen. Baraja then set up Juan Mata, who also shot too close to the keeper, before a clever free-kick routine almost prised open the Belgian team's defence. Club Brugge were causing problems of their own, and Akpala again did well to release Kouemaha, yet the Cameroon striker's lifted finish clipped the bar.
Goalless at the break, the complexion of the game changed on 51 minutes when David Silva picked up a second booking for a high challenge on Carl Hoefkens. Down to ten men, Valencia were soon behind. Kouemaha's speculative effort looked to be covered by the diving Moyá, but it bobbled over him and in.
Undeterred, Los Che went in search of an away goal and Villa came within centimetres of it on 71 minutes, only for his angled shot to hit the inside of the post and bounce to safety. It was to be Valencia's last serious effort and they will need to score at Mestalla next Thursday to have any chance of progression.