Top seeded Dutchman Fred Hemmes and Vijay Kannan, the lone Indian in the fray, bowed out of the ITF Futures tennis tournament, losing in the quarter-finals on Thursday, even as unseeded Zbynek Mlynarik moved into the last four stage.
Hemmes had an impressive start against Italian Alessandro Da Col and won the opening set 6-4, but lost ground thereafter and conceded the second set 6-7 (5/7).
With the score tied a set apiece, Hemmes failed to continue, having hurt his knee.
Vijay Kannan, the lone Indian surviving in the singles, also crashed out, suffering a 0-6, 6-3, 4-6 loss to Japanese qualifier Naoki Arimoto in one hour and fifty two minutes.
Besides Da Col and Arimoto, unseeded Zbynek Mlynarik and qualifier Marcel Felder of Uruguay moved into the semi-finals, to be played on Friday.
Kannan failed to pose any challenge to his Japanese opponent, who staged an upset by ousting third seed Aisam Qureshi of Pakistan on Wednesday, in the first set, which he lost 0-6.
The Indian rallied in the second set and broke Arimoto in the first, seventh and ninth games while losing his serve only once in the sixth game before taking the set 6-3.
In the decider, however, Kannan was broken in the fifth game. Serving for the match in the tenth game, Arimoto survived two break-points and blew two match-points before converting the third with an ace.
Unseeded Zbynek Mlynarik reached the semi-finals, getting past Jasper Smit of The Netherlands 6-4, 6-7 (4-7), 6-3 in a keenly contested tie that lasted two hours and twenty-five minutes.
Qualifier Marcel Felder (Uruguay), on the other hand, had an easy outing against Dutchman Matwee Middelkoop as he trounced his opponent in straight sets 6-3, 6-0.
In the doubles quarter finals, Hemmes's injury also cost his team (pairing Zbynek Mlynarik) a semi-final berth as Daniel Lesske (Germany) and Jasper Smit (The Netherlands) got a walk over after the former failed to take the court.