India's Yuki Bhambri put up a valiant fight against sixth seed Robin Haase before losing his first round in the singles event of the ATP Chennai Open, in Chennai, on Monday.
Ranked 217, Yuki fought well before losing 5-7, 3-6 against his Dutch rival, ranked as high as 56.
However, Prakash Amritraj made it to the singles main draw after winning his final qualifying round.
Amritraj came from a set down to edge past Briton James Ward 5-7, 6-4, 6-4 in two hours and 23 minutes.
Playing under humid conditions, Yuki fought tooth and nail in the first set but made a crucial double fault in the 12th game to give one-set advantage to his rival.
In the second set also Yuki fought well but the experienced Haase was equal to the task.
Haase led 4-3 and then shifted gear to bring in his forehand shots in to play to gain four game points to break Yuki in the eighth game, which was enough for the Dutch to hold his serve to win the match.
Yuki had four break points in the match but could not convert any of them.
"I had few chances in both the sets but could not succeed. Quite a few opportunities to break his service games. Those few points made the difference," Yuki said after the match.
In another final qualifying match, India born American Rajiv Ram also made it to the singles main draw.
Ram got the better of Kenny De Schepper of France 7-6, 4-6, 6-1 in two hours and 22 minutes.
Prakash plays Rufin Guillaume of France in the first round on Tuesday on Centre court, while Rajiv Ram is pitted against Dudi Sela of Israel (ranked 109).
"I am happy that progress is coming along. I have worked hard for 60 days for this tournament before entering the qualifying," Amritraj said.
He also revealed his desire to play for India again in the Davis Cup.
"I had my best moments of wins that have come along in Davis Cup matches. It was a great feeling. It was not a decision of AITA but the then sports minister brought in this rule (only Indian citizens to represent India in Davis Cup ties). It was his decision and now that there is a new minister and you will never know what he will do," he said.
Meanwhile, eighth seeded Go Soeda of Japan breezed through to the second round with a clinical 6-1, 6-2 win over Russian Evgeny Donskoy in just 59 minutes.
Soeda, a semi-finalist last year, started off strongly, breaking Donskoy twice in the first set. For Donskoy, ranked 81, this was his sixth straight first round defeat.