Mohun Bagan played an attacking game but failed to capitalise on the chances as they went down 2-0 to Singapore champions Tampines Rovers, who entered the quarter-finals of the AFC Cup for a third consecutive year.
Noh Alam Shah scored twice, including a goal with an acrobatic bicycle kick, to steer the home team at Tampines Stadium in Singapore.
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The Singapore international striker opened the scoring with a spectacular bicycle kick late in the first half and slotted home his second midway through the second as Tampines assured themselves of the top spot in Group F.
The visitors dominated play early on with the attacking trio of Baichung Butia, Pachau Lalam Puia and Jose Baretto causing problems for the nervous Tampines back-line.
But for all of Bagan's attacking endeavour, it was Tampines that created the better chances in the opening half.
Bagan goalkeeper Shilton Paul was called into action in the 22nd minute when Rafi Ali broke down the right flank and crossed towards the centre, where Paul clawed the ball away before it could reach a lurking Alam Shah.
Deepak Mandal gave the ball away on the left wing to Sutee Suksomkit, who whipped a high cross into the centre towards Peres de Oliviera. The cross was a bit too strong for the Brazilian playmaker who could only head it towards the penalty spot but Alam Shah sized up the ball with his back to goal before launching an acrobatic bicycle kick that gave Paul no chance.
Bagan's best chance of the half came four minutes before the break when Jose Baretto went down the left and cut the ball back from the by-line to an unmarked Mehtab Hussain, who blazed over from 10 yards.
The home side had to endure fierce pressure early into the second half as the visitors desperately looked for an equaliser.
They went close to levelling the score in the 51st minute when Lalam Puia fired in a fierce shot that hit goalkeeper Rezal Hassan and fell right at the feet of Baretto, who put his effort wide.
Bagan intensified the pressure but were caught on the break in the 66th minute when de Oliveira burst up the middle of the pitch on the counter attack. The Brazilian was surrounded by four defenders and lost possession but the ball broke to an unmarked Alam Shah, who calmly slotted the ball past Paul.
However, Alam Shah's evening ended on a bitter note as he was dismissed 18 minutes from time for a bad challenge on Douglas Santos that sparked off a melee that cleared both benches.
The Kolkata giants have collected eight points from five group matches, and they need to beat Malaysian club Pahang in the final group match.
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