Akwa United suffered a 1-2 home defeat to Banjul Hawks of Gambia, thereby putting their chances of progressing in the CAF Confederation on a tight rope.
Though the Nigeria cup holders dominated play, but goalkeeping errors cost them the game which held at Godswill Akpabio Stadium in Uyo.
The Gambians went in front against the run of play after just 11 minutes, when Akwa United goalkeeper Olorunleke Ojo spilled a free kick and Mohammed Jallow fired home the rebound.
Akwa United ought to have leveled up in the 22nd minute, but Friday Ubong missed a sitter from three yards.
Hawks doubled their advantage on 34 minutes, when Lamin Charity lobbed beyond goalkeeper Ojo, who was off his lines.
Striker Victor Mboama pulled a goal back for the home team in the 72nd minute.
Goalkeeper Yankuba Cally was outstanding for the Gambians as pulled off several big saves to ensure an important win on the road for Hawks.
The return leg match will be played in Banjul in two weeks with the overall winners advancing to the first round of the annual competition.