Zamalek failed to set one foot in the African Champions League semis after slumping to a 2-1 home defeat by South Africa's Mamelodi Sundowns on Sunday that ended their 16-match unbeaten run in all competitions.
Having already beaten Nigeria's Enyimba 1-0 away from home in the Group B opener, Zamalek could have boosted their semi-final qualification chances with a win following the dismissal of Algeria's E.S Setif by African governing body CAF due to crowd troubles.
But Sundowns were the side to go ahead in the 18th minute via a goal from Samuel Mabunda but lively midfielder Mohamed Ibrahim drew Zamalek level eight minutes before the break.
Ibrahim, one of Zamalek's best performers lately, suffered a horrific ankle injury early in the second half and his substitution had a toll on Zamalek's attacking display, with Sundowns hitting them on the break through Khama Billiat to stun the home crowd at Cairo's Petrosport Stadium.
The defeat marked the first loss for Zamalek after 16 games, which included a 12-match undefeated streak under current manager Mohamed Helmi.
Zamalek are now second of the group on three points, with Sundowns – whom the Cairo giants visit on 27 July, on top with six. Nigeria's Enyimba lie at the bottom with no points with two matches remaining for each team.
Sundowns high press trouble Zamalek
Zamalek started brightly early on, pushing forward the full-backs and pressing the South Africans backline once they lost the ball, causing them problems in the opening stages.
The first threat, however, was signaled from the visitors' midfielder Hlompho Kekana, who tested Egypt keeper Ahmed El-Shennawi from long range after just eight minutes.
Zamalek's reply then came six minutes later, with playmaker Ayman Hefni guilty of a glaring miss with the goal at his mercy following some superb footwork from right-back Hazem Emam down the right.
But the South Africans were the side to take the lead minutes later, with midfielder Tarek Hamed guilty of conceding possession before Mabunda struck on the rebound after Billiat's shot was denied by the woodwork.
Ibrahim then managed to restore parity after capitalizing on a mix-up between Sundowns keeper and the center-back to sneak in and volley home Hefni's brilliantly-lofted pass, as the ball rolled into the net after hitting the post.
Billiat wins the game
Eight minutes after the restart, defender Mohamed Koffi hit a loose ball first-time inside the area but the keeper was there to thwart the Burkina Faso center-back in Zamalek's first threat of the half.
At the other end of the pitch, it was El-Shennawi's turn to pull off a superb stop, denying the dangerous Billiat before having the crossbar to thank for thwarting David Castro's strike from inside the area.
Billiat, however, made sure he would score on his upcoming attempt, with the defensively-struggling left-back Mohamed Adel Gomaa allowing the Zimbabwean forward to beat him inside the area before the latter found the net at the near post on 67 minutes.
Winger Mostafa Fathi, who came on for the injured Ibrahim, then unleashed a powerful left-footed strike following a trademark cut-inside from the right, only for another substitute in Emmanuel Mayuka to fail to pounce on the rebound.
Zamalek remained in control in terms of possession, with the South Africans happy to sit back and protect their slender lead, which they eventually managed to do against a side who looked completely out of sorts.
