India unnerved a technically superior Qatar by taking the early lead but were eventually outplayed 1-3 in Doha in their second round qualifying football match for the 2012 Olympics.
Striker Jeje Lalpekhlua gave India the lead in the seventh minute before Qatar equalised in the 14th minute through Al Khanfan as the two sides went into the breather 1-1.
India could keep the home side at bay in the first half but they were completely outplayed in the second session, conceding two goals.
Captain Hasan Al Haydos made it 2-1 for Qatar in the 54th minute before substitute Mohammed Elneel scored in the 68th minute to complete the tally.
The scoreline could have been worse for the visitors but for goalkeeper Laxmikant Kattimani, who denied Qatari captain Al Haydos from the spot in the 11th minute and then the woodwork came to their rescue twice late in the second session.
It will be a tough task for India to further advance in the qualifying round as they now will have to beat Qatar 2-0 or better in the return leg at Pune's Balewadi Sports Complex on June 23.
India capitalised on the initial nervousness from both sides, by taking the lead in the seventh minute with Jeje finding the target to the joy of Indian expatriates in the stands at the Al Sadd Stadium late on Sunday night.
Indian captain Raju Gaikwad, who passed a fitness test just before the match, sent in his characteristic long throw from the left flank and the Qatar defence was caught napping as Jeje tapped the ball in.
Four minutes later, Kattimani saved a penalty after central defender Arnab Mondal brought down Qatari Abdul Aziz Hatem inside the Indian box. Qatari captain Al Haydos stepped up to take the penalty but his poor attempt was saved by Kattimani.
India's joy was, however, shortlived as Qatar restored parity in the 14th minute when Al Khalfan, after receiving a wonderful defence-splitting pass from Al Haydos, side stepped an advancing Indian goalkeeper Kattimani to slot the ball home.
The Indians were pushed to defending for the rest of the first half but they held fort grimly. The second half saw Qatar dominating over the Indians even more with a host of chances.
Qatari captain Haydos made amends for his missed penalty by scoring in the 54th minute with a powerful right-footer from 30 yards that settled into the left corner of the goal past a diving India custodian Kattimani.
The goal took the wind out of India's sails as Qatar made repeated raids on their citadel. Qatar got a golden chance midway through the second half but Al Ansari's shot from close could only hit the bar.
The flurry of attacks resulted in the third goal for Qatar in the 68th minute with Mohamed Elneel tapping in from close range.
Bulpin introduced Zakeer Mundampara in place of Shilton D'Silva but the Churchill Brothers playmaker couldn't really make an impact as India struggled to get hold of the ball.
The Indians pressed hard for the second away-goal but Jeje and his strike partner C S Sabeeth didn't get much support from an off-colour Lalrindika Ralte and Jewel Raja.
India did have a couple of half chances but failed to utilise them. An Arnab Mondal free header from a Lalrindika Ralte indirect freekick went straight into the hands of the Qatar keeper Saad Al Sheeb.
In injury time, Lalrindika Ralte's attempt off a free-kick was easily held by Qatar goalkeeper.
Qatar could have easily made it 4-1 but Mohammed El Neel's effort from close range hit the bar after being deflected by Kattimani.
Bulpin later admitted that his boys lost way after Qatar's second goal.
"This was always going to be a difficult match for us but we were a better team in the first half. Once we conceded that second goal we lost our way. We have lot of catching up to do," said Bulpin.
The Englishman, however, was quick to add that the 3-1 result has made the return leg in Pune interesting.
"It will be a good contest now in Pune. It will be tough but we have not given up the hopes of qualifying," said Bulpin.
