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It is 42 years since Nigerians Enugu Rangers won the now defunct African Cup Winners Cup and Ghanaians Asante Kotoko lifted the African Cup of Champions Clubs trophy 36 years ago.
Kenyans Gor Mahia and South Africans Kaizer Chiefs raised the African Cup Winners Cup 32 and 18 years ago respectively.
Egyptians Zamalek can boast of nine CAF titles, but their last success was in 2003 when they won the CAF Super Cup.
AFP Sport assesses the chances of the five former CAF trophy-holders in the two-leg play-offs with group-stage places up for grabs.
Kotoko
Kotoko, who have the unwanted CAF record of losing seven of nine finals, struggled to get past Kenyans Kariobangi Sharks after receiving a preliminary round walkover.
They now face the 2008 Champions League runners-up, Cameroonians Coton Sport, with the first leg in Yaounde.
Coton are likely to prove stronger opponents than Sharks and Kotoko will do well to leave central Africa level on aggregate.
Enugu
The draw favoured Rangers as they were paired with Lesotho outfit Bantu FC, one of the weakest of the 30 title contenders playing this weekend.
Bantu were demoted from the Champions League to the Confederation Cup without winning any of their four matches and it is hard to imagine them shocking the Nigerians, at home or away.
In Godwin Aguda and Bright Silas, Enugu have attackers who scored three goals each to help eliminate Ethiopians Defence Force and Algerians USM Bel Abbes in qualifiers.
Gor
The Nairobi club have been steadily improving in Africa, becoming the first Kenyan qualifiers for the Confederation Cup group stage last year.
Gor almost achieved an even greater success in the current Champions League, but conceded a late goal away to Nigerians Lobi Stars and missed out on a group place.
They host Cameroonians New Star, whose five-goal striker Junior Ngongang is the leading scorer in this Confederation Cup.
Chiefs
Chiefs, who have won 53 domestic trophies since being formed 49 years ago but only one in Africa, will lack injured goalkeeper Itumeleng Khune away to Zambians Zesco United.
His absence was sorely felt last weekend with a blunder by Namibian stand-in Virgil Vries gifting a undeserved victory to Mamelodi Sundowns in a key league match.
Zesco sharpshooter Lazarous Kambole, whose five-minute hat-trick last season was the fastest in a CAF club match, poses a major threat to the Soweto outfit.
Zamalek
After several seasons in the doldrums and being overshadowed by arch rivals Al Ahly, the Cairo White Knights are leading the Egyptian title race under Swiss coach Christian Gross.
They took this good form into Africa last month to slam seven goals past Chadians ASCOT in the home leg of a qualifier with Congolese Kabongo Kasongo bagging a brace.
Away to Moroccans Ittihad Tanger this weekend, Zamalek will probably be satisfied to avoid defeat, then use home advantage to emerge overall winners.
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