Manuel Jose ended his title-strewn career as Al-Ahly coach disastrously when the Egyptian giants were dumped out of the African Confederation Cup by Santos in Angola on Sunday.
Ahly, winners of the African Champions League a record six times, took a 3-0 lead into the return match and even the absence of star midfielder Mohamed Aboutraika was not expected to prevent them reaching the group phase.
But a Santos team competing in Africa for the first time this year had other ideas and triumphed 3-0 in Luanda to level the aggregate score before winning the fourth-round tie 6-5 on penalties.
Among those who failed from the spot for Ahly was Angola-born striker Flavio Amado, whose agent claims he is quitting the Cairo ‘Red Devils’ for a three-year contract with Saudi Arabian outfit Shabab.
Bebucho put the Angolans ahead mid-way through the first half, Milex set up a thrilling finish with a second goal as the game entered the closing stages and Saul struck the crucial third two minutes from full-time.
All the goals were brilliantly executed by a team who scored four goals each in previous home encounters against USM of Gabon and Union Douala of Cameroon having received a first round bye.
Bebucho strode forward before unleashing an unstoppable 30-metre shot past goalkeeper Ramzi Saleh, Milex volleyed a loose ball into the net from close range and Saul clinically sidefooted home a cross.
Success for Santos completed a wonderful weekend for the oil-rich southern Africa nation in the second-tier African club competition, as Primeiro Agosto eliminated holders CS Sfaxien in Tunisia on Saturday, also after a shootout.
Ahly have campaigned in Africa regularly since 1975 and this was only the fourth time they had suffered a three-goal loss, with Mouloudia Alger of Algeria, Hearts of Oak of Ghana and Al-Hilal of Sudan inflicting the other defeats.
The heavy reverses against Mouloudia and Hearts came three decades ago while Hilal triumphed two years ago in Omdurman against a club that claims 40 million supporters in Egypt and the Middle East.
It was a sad exit for Jose, who stays in Luanda to take over a struggling Angolan national team from June 1 with the task of building a team capable of using home advantage to win the 2010 African Nations Cup.
The 63-year-old Portuguese led Ahly to four of their six African Champions League titles and many African media observers consider him the greatest foreign coach to have worked at club level on the continent.
Primeiro lost 2-0 to Sfaxien only to convert all their post-match penalties and win the shootout 5-4, while Stade Malien of Mali outplayed Al-Ittihad Khemisset of Morocco 3-1 in Bamako to advance 4-2 on aggregate.
Another five ties in the final qualifying round will be decided later on Sunday before the mini-league phase kicks off in mid-July.