Ace shooter Jitu Rai failed to make it to the final of the men's 10m Air Pistol at the International Shooting Sport Federation World Cup (Rifle/Pistol), in Munich, on Monday.
Tejaswini Sawant in the Women's 50m Rifle 3 Positions event, also fell short of qualifying mark.
Jitu finished 10th overall while Tejaswini secured 15th position.
Among his five World Cup medals in this event, only once has Jitu shot higher than Monday's 581, to qualify for the finals. He was in the hunt till the last four shots, but two 9s in the 57th and 58th shots proved crucial in the end.
Turkey's Tugrul Ozer was the 8th to qualify with a score 582 but with significantly lesser number of inner 10s than Jitu.
Jitu's team-mates in the event, fellow Olympian Prakash Nanjappa and youngster Anmol Jain both finished with identical scores of 576 and in 34th and 36th positions respectively.
Gold in the event went to 19-year old Ukranian youngster Pavlo Korostylov, who landed his first ever World Cup Gold in the senior ranks. Japanese former World Champion Tomoyoki Matsuda won Silver and Korean legend Jongoh Jin won Bronze.
In the Women's Rifle 3 Positions, Tejaswini shot a high of 199 out of 200 in the prone position, but even that was not enough as her qualification round score of 584 was two behind 586, recorded by as many as three final qualifiers.
The other Indians in the fray, N. Gaayathri finished 38th with a score of 579 while Elizabeth Susan Koshy shot 576 to end in 55th place.
On Sunday, India's challenge in the two medal events of the day- both for men, the 50m Rifle Prone and the 25m Rapid Fire Pistol was also restricted to the qualifying stages.
In 50m Rifle Prone, Sushil Ghaley shot 622.7 to finish 31st, Chain Singh 622.1 for 37th place and Sanjeev Rajput managed 616.6 to end in 65th position overall.
In the 25m Rapid Fire Pistol, Neeraj Kumar was the best Indian finisher in 18th place shooting a score of 578. Harpreet Singh shot a point less to secure 21st spot while Olympian Gurpreet Singh ended in 31st position with a score of 572.
Tuesday is the fifth and final competition day of the World Cup and will feature the Women's 10m Air Pistol and Men's 50m Rifle 3 Positions finals. Former World number one Heena Sidhu and three time Olympian Sanjeev Rajput will lead India’s challenge in the two events.