Enyimba continued their poor run at the Gold Cup pre-season tournament in Ijebu Ode following a 1-0 defeat against Crown FC on Tuesday.
Friday Jacob scored the winning goal for Nigeria National League’s Crown on the half hour mark.
It was the Peoples Elephant’s second defeat in the competition and put their qualification for the semi-finals in doubt.
Former Nigeria Professional Football League champions Kano Pillars also beat Niger Tornadoes 1-0 to maintain their unbeaten run in the competition.
Adamu Mohammed netted the winner in the 31st minute.
Nigeria Nationwide League side FC Ebedei shocked Sunshine Stars, edging out the Owena Waves 2-0 in the other game.
Earlier in the day, Remo Stars beat non-League club FC Yobo 3-2 in a highly entertaining encounter.