Zamalek lose 1-0 at home to Wydad in the African Champions League (Ahram)
Midfielder Yahya Jabrane converted a penalty three minutes into the second half following a bizarre handball by defender Mahmoud El-Wensh as Wydad completed the double over Zamalek, having also won 3-1 in Casablanca last month.
The defeat spoiled the first appearance of Jesualdo Ferreira in Zamalek's dugout after the veteran Portuguese coach returned to the club he led to a rare domestic double in 2015.
The angry home supporters made offensive chants against Zamalek's players towards the end as the team face a near-certain exit from the Champions League group stage for the second straight season.
The five-time African champions, who have not won any of their first four games, lie third in Group D with two points, five behind Angola's Petro Atletico, who have a game in hand, and seven adrift of leaders Wydad, who moved within touching distance of a place in the last eight.
Should Petro Atletico beat fellow Angolan side Sagrada Esperance (one point) on Saturday, Zamalek will officially wave goodbye to Africa's blue-riband club competition, which they last won in 2002.
Zamalek looked largely toothless throughout, with Wydad's compact defence leaving them with little room to operate in the final third.
With the likes of Achraf Bencharki and Emam Ashour, their primary sources of creativity, looking sluggish, Zamalek struggled to hit top gear although they still created a couple of goal-scoring chances through crosses in the first half.
Playmaker Youssef Obama rose above his marker following a left-wing cross from Ahmed Fattouh after seven minutes but his header was parried by keeper Reda Tagnaouti, who produced a superb reflex save to thwart Ahmed Zizo's attempted follow-up effort.
Tagnaouti was at fault in the 19th minute though when he mis-judged a free-kick from Zizo, only for off-form striker Omar El-Said to miss an open net with a bouncing header at the far post.
That was as good as it got for a below-par Zamalek side, whose woes were compounded when Wydad were gifted a penalty out of the blue early in the second period.
El-Wensh inexplicably stooped to head clear an innocuous free kick, only for the ball to come off his outstretched arm with the referee instantly pointing to the spot.
Jabrane's composed penalty found the top corner past keeper Mohamed Abou-Gabal and Wydad easily dealt with Zamalek's feeble attempts to equalise, with the angry chants ringing out at the Cairo International Stadium in the dying minutes and after the final whistle.
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