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Enyimba and Remo Stars crashed out of the CAF Champions League on Sunday on a bleak day for Nigerian clubs.
Two-time title-holders Enyimba were held 0-0 in Aba by Libyan opponents Al Ahly Benghazi, who won the preliminary tie 4-3 on aggregate after snatching an added-time winner in the first leg.
Champions League debutants Remo missed three consecutive penalties to lose a shootout 3-2 after winning 1-0 at home and drawing 1-1 on aggregate with Ghanaian outfit Medeama.
Enyimba were one of two former champions to bow out after the first qualifying round with V Club from the Democratic Republic of Congo the other losers.
Former title-holders ASEC Mimosas of the Ivory Coast, Etoile Sahel of Tunisia, FAR Rabat of Morocco, Hafia of Guinea and Orlando Pirates of South Africa secured places in the last-32 round.
Enyimba, back-to-back African champions in 2003 and 2004, recently appointed former Arsenal and Nigeria star Nwankwo Kanu as chairman and were confident of making an impact in Africa.
But after scoring three times in the intimidating fortress of Benghazi, they could not manage even one goal at home. A 1-0 win for Enyimba would have sufficed to win the tie.
FROM VILLAIN TO HERO
Unlike Europe, who scrapped the away-goal rule in club competitions two years ago, it still applies in Africa.
Benghazi, whose best Champions League performance was eliminating then title-holders Al Ahly of Egypt in a 2014 qualifier, now face ASEC for one of 16 group place.
Medeama goalkeeper Felix Kyei was the villain who became a hero as his club secured another west African showdown, this time with Horoya of Guinea.
He conceded an own-goal after a corner midway through the second half to gift Remo a 1-0 second-leg win, then saved three shootout spot-kicks to break Nigerians hearts.
After both sides had converted two penalties, Jonathan Sowah raced forward and fired his kick past Kayode Bankole to take Medeama through.
V Club were undone by a compatriot with an early second half goal from DR Congo-born Obed Mukokiani earning Angolan visitors Primeiro Agosto a 1-1 draw in Kinshasa and a 2-1 overall win.
Malian club Real Bamako, back in the Champions League after a four-year absence, upset Cameroonians Coton Sport 2-0 in Garoua with Nouhou Cisse scoring in each half.
The first leg in Mali had ended goalless, and the reward for Real is a tie against Mauritanians Nouadhibou.