Bangladesh trailed by three runs in a thrilling match against the West Indies, which ended the Tigers' hopes of reaching the World Twenty20 semifinals with three consecutive defeats.
To chase 143 runs to win, Bangladesh need 13 runs in the last over as Liton Das and Mahmudullah put on a 40-run stand in Sharjah on Friday.
But after Liton's fall in the last over, the required runs became heavy on the captain and new batsman Afif Hossain, who failed to connect properly and broke the hearts of Bangladeshi fans.
On a tough surface, Bangladesh opener Mohammad Naeem (18) and his great pair lost to Shakib Al Hasan (9), reaching 29 for two at the end of the powerplay.
Liton was cautious in the beginning, then Akel Hossain gave a breakthrough to look at the end before adding 31 runs for the third wicket with Soumya Sarkar (18).
Determined to make a stand, Liton scored another 30 runs with Mushfiqur Rahim, whose clever paddle dropped his 8 runs again as Bangladesh were bowled out for 90 for four in the 14th over.
Mahmudullah hit a six and hit two boundaries and a six to keep the momentum going.
After hitting a six, Dwayne Bravo's revenge for the ball and Liton's wicket, Bangladesh took five wickets in the last over of Andre Russell's game to ensure the Caribbean team's first victory in the tournament.
Earlier, the West Indies batsmen scored 142 runs for 7 wickets in a challenging surface against Bangladesh.
The Caribbeans were hampered by Roston Chase's (39 off 46 balls) and Nicholas Puran's 40 off 22-ball attack.
Deciding to bowl, the Tigers dominated the first half with three wickets in hand, restricting the West Indies to 48 for three in the first 10 overs, while the Caribbeans managed just two boundaries.
Mahedi Hasan, who took two wickets in the first innings, got two catches to give Bangladesh the lead but he swallowed both.
In a bold move, Kieron Pollard (14 not out) retired himself to get Puran out and turn everything around.
Chase hit four sixes and a boundary to give Chase a half-century and Seema Taskin Ahmed struck out two in a row.
After dropping another sitter in Afif Hossain Death, Pollard came back and gave the Tigers over a rope to give them a cracking target to survive in the tournament.
Later, Nicholas Puran said: “It is difficult to manage all the players, but everyone gives me full support. All hands on the field deck. Unfortunately we didn’t really get all our catches, but there was faith.
“We have supported our experience to stop the game. (Not using chase) We had confidence in experienced bowlers. Akil bowled really well and did it again today. The length behind that wicket was tough.
“(Russell last over) He’s a great player and a death sentence for us. (Regarding Pollard's health) She looks good, the medical team is still working with her but she is fine. You can see why he is a great leader, he came back with a six in the last over. We will try to be one in the future. "
In his post-match presentation, Mahmudullah said, "I think Liton's wicket was very important because we were both set. If it's six ... this is probably an advantage if you have a long fielder. That said, the bowlers did quite well but we missed a few chances which cost 10-15 runs.
“We tried (to get tough on top) but the wicket wasn’t where you could hit. It was hard to score when you bowled at back off length. The bowlers did well, but it's batting… but it was a close game, we can't blame the batsmen or the bowlers, in T20 cricket you have won some matches, lost some. (Dropping catch) It's a problem, we need to do better.
Against Australia and South Africa - and virtually no way to cross the pool stage - Bangladesh is now at the bottom of the table.
They will face Australia on November 2 at the Dubai International Cricket Stadium.
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