A lacklustre Dempo suffered a 1-2 defeat to Syrian side Al Maged in their Group E AFC Cup match in Damascus on Tuesday night.
Dempo, who had beaten their opponents 1-0 at home, were outclassed by the Syrian side and could have lost by a bigger margin had not goalkeeper Abhijit Mondal saved at least half a dozen shots on target at the Al Abbassiyin Stadium.
Dempo are now second behind Al Maged with seven points from five matches and have to win their last group match against bottom-placed Al Faisaly of Jordan on May 19 in Margao, Goa.
Al Maged, with 10 points from five matches, are through to the quarter-finals with one match left -- against Bahrain's Al Muharraq (six points) on May 19.
Abdulhadi Al Hariri opened the scoring for the Syrian side in the 40th minute and Kenan Al Nama made it 2-0 in the 63rd before Roberto Mendes Silva pulled one back for Dempo in the 67th minute.
Mondal first blocked a powerful shot from Al Maged's Senegalese midfielder Dame Junior Gaye in the sixth minute and then denied Bashar Al Kaddour a few minutes later.
Two other saves off the efforts of Samer Aouad and Al Zino kept Mondal busy but the Al Maged attack was too frequent to deny them for long and the Syrian side forged ahead five minutes from the breather with Al Hariri connecting Al Zino's cross from right with a powerful header.
Three minutes later, Al Hariri was denied what could have been his second goal by a diving Mondal.
Dempo played better in the second half and Silva's free-kick in the 54th minute flew inches above the woodwork.
Al Maged made it 2-0 three minutes after the hour mark when Al Nama's shot from 20 metres found the top right corner of the Dempo net.
Barely a minute later Al Zino found himself with only the goalkeeper to beat but Mondal was once again Dempo's saviour.
The Goan side pulled one back in the 67th minute when Silva met a cross from the right with a powerful header that flew past Al Maged goalkeeper Samer Saaid.
Al Maged nearly regained their two-goal cushion in the 79th minute as an Ali Diab header slammed against the crossbar.
Dempo coach Armando Colaco conceded that Al Maged were deserving winners.
"The result is convincing as Al Maged had the better chances in the game. Our mission is hard now as we have a game against Al Faisaly on the last match day," Colaco said.