A below-par Zamalek side failed to give new boss Alex McLeish a winning start after suffering a stinging 3-1 Egyptian league defeat at the hands of a 10-man El-Entag El-Harby at Petrosport Stadium on Thursday.
Appointed as Zamalek boss a few days ago, Scottish manager McLeish did not enjoy the best of debuts at the helm of his new club – thanks to a largely dismal display by the league holders.
Entag took the lead in the first half through Salah Amin, before Zambian striker Emmanuel Mayuka leveled the score 10 minutes later.
The hosts then made it two through Amin again with 20 minutes left, before defender Mahmoud Fathallah compounded his former side's woes with a late penalty in the 84th minute.
Entag defender Loay Wael was sent off on the stroke of halftime for a second bookable offence, leaving Zamalek with a numerical advantage all through the second half .
The Cairo giants remain in second spot on 38 points, six adrift of leaders Ahly, while Entag have climbed into fifth on 31.
Entag defender dismissed
The match kicked off with Zamalek not looking quite in good form, with Ayman Hefni, Mahmoud Kahraba and midfielder Omar Gaber obviously out of sorts.
It was just 16 minutes into the opening period when the hosts took the lead, as Amin scored on the rebound from inside the six-yard box after Egypt keeper Ahmed El-Shennawi spilled Fathallah's free kick.
Zamalek sprang into life after the concession, with overlapping full-back Mohamed Adel presenting their main source of danger down the left.
After a series of inaccurate crosses, Adel finally managed to set up Zamalek's equaliser after Mayuka's directed header beat keeper Amir Abdel-Hamid in the 26th minute.
Entag striker Amin then saw a header following a corner go narrowly wide , in what was the home side's major chance after the leveler.
Entag defender Wael was then dismissed for a second booking, forcing the military side to complete the game with ten players.
Entag score against run of play
Surprisingly, it was the 10-man Entag who looked determined after the break – with the Whites needing nine minutes to pose real threat on goal.
The largely peripheral Kahraba was the one involved this time, seeing a header agonisingly denied by the woodwork following a left-wing cross from Adel.
Minutes later, Egypt international Kahraba was guilty of another glaring miss from inside the area after blasting high when it looked easy to score.
But it wasn't only Kahraba who was unlucky on the night, as Mayuka was again frustrated by the woodwork after his one-on-one effort hit the post.
And much to Zamalek's frustration, it was just three minutes later when Entag star striker Amin made it 2-1, after a cross from the right eventually found the forward who easily slotted past El-Shennawi at the near post.
Manager McLeish then moved to make changes, substituting Kahraba by striker Bassem Morsy, a change that came seven minutes after skipper Hazem Emam made way for Shikabala.
Shikabala was not any more fortunate than his teammates, as a right-footed half-volley with 10 minutes remaining was blocked by understudy keeper Amer Amer – who replaced the injured Abdel-Hamid.
But as Zamalek desperately searched for the equaliser, Entag - against the run of play - scored again– with Fathallah making it three from the spot after Amin was brought down by full-back Adel inside the area.
With the referee giving a 10-minute stoppage-time, Zamalek continued to pile up pressure, with sub Mostafa Fathi spurning a golden chance from inside.
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