Nigeria's last team standing in this year's CAF Champions League, Rangers International FC of Enugu failed in the bid to cancel out Zamalek of Egypt 3-0 advantage from the first leg in Cairo.
Though the Flying Antelopes defeated Zamalek 2-1 yesterday at the Nnamdi Azikiwe Stadium in Enugu, it was not enough to guarantee the Nigerian league champions passage to the money spinning group stage. Zamalek progressed on 5-3 aggregate.
Nigeria's other representative in the CAF Champions League, Rivers United had earlier suffered similar fate on Saturday with a humiliating 0-4 loss to El Merriekh of Sudan in Khartoum. That defeat cancelled out the 3-0 advantage achieved by the Rivers State owned team last week in Port Harcourt.
By this result, both teams have dropped into the play-off of the second tier CAF Confederation Cup.
At the Nnamdi Azikwe Stadium, Zamalek stopped all the early incursions made by Rangers despite gaining control of the game.
Tope Olusesi fired the home side into the lead on the stroke of half-time thus needing two more goals to reach the group stage of the champions league.
Zamalek goalkeeper Mahmoud Abdel Rahim, who is better known as Genesh, pulled off a double save after restart as Rangers continued their dominance.
With his side trailing, Mohammed Helmy, the Zamalek coach, introduced striker Bassem Morsy in the 62nd minute as the visitors looked to equalise.
The Egypt international made an immediate impact as he scored to level matters against Rangers eight minutes later.
However, Rangers pushed forward in search of another goal in order to restore their lead and they were awarded a penalty with fifteen minutes left on the clock.
Godwin Aguda then stepped up and fire past Genesh to make it 2-1 for Rangers. But Zamalek stood firm at the back till the dying minutes. Rangers could not celebrate the 2-1 victory as it could not guarantee them progress.
Elsewhere yesterday, defending champions, TP Mazembe of the Democratic Republic of Congo suffered a shock exit from the competition losing on the away-goals ruling to Zimbabwe's CAPS United in Harare.
Mazembe were under pressure after being held to a 1-1 draw in the first leg of their last-32 tie at home in Lubumbashi last weekend
The away-goal proved to be crucial for CAPS United who withstood the pressure from Mazembe in the second leg in Harare, earning a 0-0 draw.
Mazembe, who won the African Champions League in 2015, were left frustrated by the Zimbabwean underdogs in their search for a goal.
As in the first leg in Lubumbashi, CAPS United's goalkeeper, Edmore Sibanda, stood firm to deny the DR Congo giants a chance to score.
Like Rangers and Rivers United, Mazembe has now dropped into the Confederation Cup play-off round, where they will look to defend the title they won in 2016.
The result is a huge accomplishment for CAPS United of Zimbabwe who has returned to the Champions League after an 11-year absence.
The Zimbabwean team will now enter the group phase of the tournament which has been expanded from eight to 16 clubs.