Imran Sahib and Miljan Mrdakovic both saw red as the S.League champions were beaten 2-1 by Hong Kong side South China after the tie ended 1-1 in regulation time
Despite having a numerical advantage for majority of the first-round play-off tie a mixture of poor finishing and an inspired performance by Stags custodian Hyrulnizam Juma’at kept the visitors at bay right up to extra time.
Andrew Barisic had broken the deadlock for the Hong Kong champions in the first half, but Tampines equalised midway through the second period. However, the visitors proved too powerful in extra time and Barisic scored his second in the first half to send them through to the next round of the play-offs.
South China dominated the opening exchanges, but it was the evergreen Aleksandar Duric who had a chance to give his side the lead.
He got his head to Shahdan Sulaiman’s free-kick, but could only direct the ball straigh into the arms of goalkeeper Yapp Hung Fai. Two minutes later, it was Kunihiro Yamashita's turn as he headed a corner straight at Yapp.
South China looked threatening going forward but did not trouble the Tampines goal, until they opened the scoring on 21 minutes.
Lee Wai Lim beat the offside trap down the right and squared the ball to the unmarked Barisic, who easily slotted it home.
Tampines’ best chance came after the half hour mark when Norihiro Kawakami’s header was cleared off the line after Duric’s knockback from a corner.
But their task to rescue the game took a major setback a few minutes later when Japanese referee Iida Jumpei sent off midfielder Imran Sahib for a second bookable offence.
Nevertheless, the Stags hung on and rode their luck as the Hong Kong side started the second half menacingly, with Sasa Kajkut, Chan Siu Ki and Leung Chun Pong all firing over from long range.
Tampines regained the initiative after an inspired double substitution as Luis Closa and Jamil Ali came on, with the former turning architect for the equaliser.
The Paraguayan found Shaiful Esah on the left just after the hour mark and the full-back crossed for marquee signing Miljan Mrdakovic, who stabbed home under pressure.
A few minutes later, Closa released Mrdakovic through on goal, but his rushed shot from 20 yards bounced wide.
Kwok Kin Pong then went close for the visitors on 75 minutes as his shot on the edge of the penalty box took a wicked deflection, but Hyrulnizam got a fingertip to it.
Both sides tried in vain to search for the winner as full time approached but to no avail as extra time was needed.
Barisic hit the upright with a brilliant acrobatic effort towards the end of first half extra time, but scored the winner immediately after that.
Kajkut squared the ball from the right and Barisic hit a first-time effort into the bottom corner to send the vocal bunch of away fans wild
The Stags' misery was compounded towards the latter stages when Mrdakovic got sent off for a second bookable offence to leave them seeing out the game with nine men.
Salim Moin’s competitive debut for the S.League champions proved to be too tall an order for his team, who now have to look forward to the Charity Shield against Home United on February 21.