Egypt's Ahly failed to ensure their progress to the Confederation Cup semis with one match to spare in Group B after a lackluster display saw them lose 1-0 away to Zambia's Nkana on Saturday.
The Red Devils, who are seeking to become the first Egyptian side to win Africa's secondary club competition, were undone by a dubious second-half penalty from Billy Mwanza to suffer their first group-stage defeat.
Ahly needed only a draw to book a last-four berth but they were hugely disappointing, failing to carve out openings on a muddy pitch in Kitwe.
The Cairo giants are still on top of the group with 8 points, one ahead of Nkana and three clear of Tunisia's Etoile Sahel.
If Etoile beat Ivory Coast's Sewe Sport (three points) later in the day, their last meeting with Ahly in Cairo will be decisive in determining who would qualify from the group.
Chances were at a premium in a drab first half, with Ahly adopting a cautious approach to get the point they needed to advance.
The only goal-scoring chance in the first period fell to Nkana's Ronald Kampamba, whose close-range volley went just over the bar with the goal at his mercy.
Nkana opened the scoring in controversial fashion when Mwanza sent keeper Sherif Ekramy the wrong way from the spot after a Nkana forward tumbled under the slightest of challenges from Ahly full-back Sabri Rahil in the 51st minute.
Despite falling behind, Ahly remained out of sorts and rarely threatened the hosts, with the introduction of striker Emad Meteb, forward Moussa Yedan and winger Walid Soliman doing little to spur them into action.
Soliman squandered Ahly's best chance with 13 minutes remaining when he sneaked in behind his challenger to get a touch to a long ball that sailed past the advancing keeper but a Nkana defender reacted swiftly to clear the ball before it crosses the line.
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