The first half was cagey and featured missed chances by Mohammed Musa, Edmilson Junior and Dudu for Al Duhail as well as Cedric Amissi for the Buraidah based side. Deep into stoppage time in the first half, Cassio expertly denied Almoez Ali who struck from the left.

Junior threatened 55 minutes in, and after a break by his side, the Belgian cut inside from the left flank beating two players before curling an effort in from range that Cassio gratefully clutched into his arms.

The match exploded into life in the final 10 minutes, with Al Duhail missing a golden chance to open the scoring through Ismail Mohammed, who was through on goal with just the keeper to beat and chipped, but substitute Saad Yaslam managed to reach the ball and clear off the line.

A bandaged Duke then dramatically sealed the tie for Al Taawoun after breaking free from his marker in the area to meet Sultan Mandash’s corner and put the ball past Al Bakri.

The result sees Al Duhail crash out of the competition, while Al Taawoun qualify to the Round of 16 for the first time in their history.

Persepolis' 4-0 win over Sharjah in the other Group C fixture means Al Taawoun will face fellow Saudi side Al Nassr in the next round while Persepolis play Al Sadd.