Qarabag scored a dramatic stoppage-time winner to end Eintracht Frankfurt’s hopes of reaching the Champions League play-offs and keep their own qualification chances alive.

Behlul Mustafazade made history by becoming the first Azerbaijani player to score in the competition, finding the net with the final kick of a chaotic and thrilling encounter. The result leaves the hosts 18th in the standings with 10 points, a position that almost certainly secures them a place in the play-offs.

Eintracht Frankfurt, meanwhile, are eliminated from the tournament after collecting just four points from seven matches, leaving them down in 33rd place.

The German side travelled to Azerbaijan following the dismissal of head coach Dino Toppmoller on Sunday, after managing only one win in their last nine games.

Frankfurt endured a nightmare start to the match as Colombian forward Camilo Duran opened the scoring for Qarabag inside the first four minutes, netting the first of his two goals on the night.

However, the visitors responded well. Can Uzun equalised before Fares Chaibi converted a second-half penalty to put Frankfurt ahead, raising hopes of a turnaround. But their defensive weaknesses were once again exposed.

For the second time in the match, a powerful forward run by Elvin Cafarquliyev created the chance for Duran to score, restoring parity for Qarabag. Then, with the final action of the game, Mustafazade struck the decisive goal, sealing a memorable victory and easing the pressure ahead of their trip to Liverpool on 28 January.