Mahindra United failed to capitalise on chances that came their way and went down 1-2 to Lebanon's Al Nejmeh club in the first leg of the AFC Cup quarter-final.
The Mumbai outfit will take on the Lebanon club at home on September 18 before playing the away leg a week later.
Al Ittihad of Syria rode on a double strike by Abdulfatah Alagha and pumped in two goals in the dying minutes to drub East Bengal 4-1 in their Group D AFC Cup opening match at the Salt Lake stadium in Kolkata on Wednesday.
Mahindra United drew with Al Nejmeh 3-3 in the away match in Beirut and lost the AFC Cup tie on 5-4 aggregate.
Federation Cup champions East Bengal suffered their second consecutive defeat in the AFC Cup after going down 0-3 to formidable Lebanese side Al Nejmeh in a lop-sided football match in Beirut.
The Indian National Football League champions beat Bangladesh's Brothers Union to keep alive their chances of making it to the quarter-finals.
India brightened its chances of qualifying for the AFC Under-16 football championship by beating Lebanon 3-0 at Dammam in Saudi Arabia on Thursday.