Holders Ahly of Egypt produced another error-ridden display to suffer a 3-2 African Champions League loss at home to Ahly Benghazi that sent them packing on Saturday, denying them a chance to win an unprecedented third consecutive title.
The Cairo giants were eliminated with a 4-2 aggregate defeat, having slumped to a 1-0 first-leg defeat in Tunisia.
They still have a chance to add to their 19 continental titles, a world record, as they will feature in the African Confederation Cup, the continent's secondary club competition.
Saturday's defeat by Benghazi at Cairo's Air-Defence Stadium marked the first time Ahly bow out in the round of 16 since they lost to Nigeria's Kano Pillars at the same stage in 2009.
It is also their ninth loss in 18 matches in all competitions this season, a dismal record under coach Mohamed Youssef who reports suggest will be shown the door.
Tarek El-Ashry, the Egyptian coach of Benghazi, proved Ahly's nemesis again, having led his former side Haras El-Hodoud to some crucial cup victories over the Red Devils in recent years.
Ahly, who are also struggling in the domestic league, seemed on course to overturn the first-leg deficit when their relentless pressure allowed central defender Mohamed Naguib to score a rare goal eight minutes before the break.
But Abdulrahman Fetori levelled the score shortly after from the spot and further second-half goals from Farag Abdel-Hafiz and Moataz El Mahdy stunned the hosts and effectively killed off their hopes of reaching the group stage of the competition they had won the past two seasons.
Ahly, who netted a consolation through promising striker Amr Gamal, also had to play with ten men for around 25 minutes following the second-half dismissal of right-back Ahmed Fathi, who received a straight red card for a reckless, two-footed lunge on an opponent.
Gamal played as a lone striker in front of three attacking midfielders in Gedo, Abdallah El-Said and Burkinabe Moussa Yedan.
Unlike the first leg when two defensive-minded central midfielders hardly fed the forwards, the presence of Mahmoud Trezeguet in the centre drove Ahly forward as Benghazi defended in numbers.
A lively Ahly side laid siege to Benghazi's area in the first half, moving the ball around smoothly and creating a couple of goal-scoring opportunities in the first 22 minutes.
Yedan chested down a poor defensive clearance and fired a right-foot volley that went just over the crossbar from inside the area and a low Gamal shot missed the target with the goal at his mercy after a follow-up effort.
Ahly's pressure paid dividends on 38 minutes when El-Said ran down the left and cut the ball back to Naguib, whose angled shot went into the bottom corner of the net.
However, Ahly's celebrations were short-lived as a clumsy challenge by Hossam Ashour on Edward Sadomba, who neatly controlled a long ball in the area, three minutes later prompted the referee to point to the spot and Fetori made no mistake with a powerful drive.
Ahly were caught on the break in the second half as Benghazi's efficiency was on full display.
Abdel-Hafiz put the visitors in front with a 25-metre thunderbolt that went in off the bar in the 52nd minute and El Mahdy toyed with two challengers in the area to curl a delightful shot into the far corner for the third six minutes later.
A free header by Gamal in the 75th minute was too little, too late as Ahly still needed three more goals to advance, with another mediocre display renewing fan calls for a squad overhaul following last year's retirement of talismanic playmaker Mohamed Abou-Treika.
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