Ramkumar Ramanathan squandered his chances in the deciding set while Sasikumar Mukund went down fighting in his match as India's singles challenge ended in the first round at the Tata Open Maharashtra here on Tuesday.
Coming into the main draw from the qualifying route, Ramkumar lost 3-6 7-5 6-3 to Spanish world number 62 Pedro Martinez in two hours and 28 minutes.
Mukund, who got a wild card entry as the country's best-ranked player at number 340, matched Flavio Cobolli stroke for stroke from the baseline but his Italian opponent got the points when it mattered and won 6-4 7-5 in one hour and 38 minutes at the centre court.
Teenager Manas Dhamne and Sumit Nagal, who had also got wild card entries, had lost their first-round matches on Monday.
Tata Open is India's biggest ATP event but the players have not been able to cash in on the changes that are coming their way.
In the other matches of the day, Dutch player Tim van Rijthoven knocked out Moldova's Radu Albot 6-4 6-4 while the eighth seed Russian Aslan Karatsev made short work of Pablo Andujar 6-1 6-3.
In an all-Indian affair, the pair of Jeevan Nedunchezhiyan and Sriram Balaji, who came in as an alternate team, beat wild card entrants Purav Raja and Divij Sharan 6-4 6-3.
Ramkumar's serve and volley game worked wonders in the opening set but he allowed his rival to make a comeback. Martinez moved Ramkumar around with deep returns and often landed shots near the Indian's feet, making it tough for him to pick up half volleys. His passing shots were a delight to watch, and they made a lot of difference to the outcome of the match.
Egged on by the crowd, Ramkumar fought his heart out when Martinez was serving for the match but hit a forehand long at 30-all. Ramkumar saved a match point when his rival netted a forehand. Martinez eventually closed the match with a deft volley winner.
Ramkumar struggled with his first serve initially but still dished out the serve and volley style in the match. Most of his points came in that fashion. Martinez relied a lot on his forehand and few of his returns did trouble, Ramkumar.
On a hot and sultry afternoon, the first game of the match lasted almost 10 minutes with Ramkumar dropping serve after playing five deuce points. Martinez returned low straight onto Ramkumar's shoes and he could not pick up the half-volley, burying it on the net.
Martinez though could not build on the advantage and dropped his own, struggling to contain his unforced errors. The Indian came up with splendid cross-court backhand winners in the fourth game to get his first break of the match. A comfortable hold put him firmly in the driver's seat, opening up a 4-1 lead.
An intense game followed in which Martinez saved three breakpoints, smartly using the drop shots but Ramkumar fired a screaming backhand winner past his rival to go up 5-1. Serving for the set, Ramkumar dropped his serve with Martinez running him around and passing him thrice.
Ramkumar fired an ace to earn two set points and converted the first when Martinez netted a backhand return. The Indian had plenty of chances to draw blood early in the second set but missed four break points, including two in the third game, and could not convert.
It was on serve till the 11th game. Ramkumar was one point away from the tie-break when Martinez found a fantastic passing winner from the corner to make it a deuce. A crushing cross-court winner gave Martinez his first set point and Ramkumar double-faulted to give the Spaniard a chance to keep the match alive. Once Ramkumar lost break chances in the decider, Martinez was all over.