Shooter Abhinav Bindra narrowly missed out on a medal in his Olympic swansong as the men's hockey team suffered a late 1-2 defeat to Germany, while the women's hockey side was thrashed 0-3 by Britain in group stages in a disappointing Monday's campaign for India at the Rio Games.
Adding to the disappointment was archer Laxmirani Majhi, who crashed out in the Round of 32 eliminators.
Bindra, India's sole individual Olympic gold medallist, finished fourth in the final of the men's 10 metre Air Rifle final at the Olympic Shooting Centre on Monday.
Bindra started well, but a couple of wayward shots cost him dearly as he lost in the bronze medal play-off to finish fourth with a total score of 163.8.
Monday's disappointment will see the curtains come down on the glittering career of the 2008 Beijing Olympics gold medallist as he had earlier announced that he will retire after the Rio Olympics.
"I think I did my best but a medal was not to be. It was a tough field. Somebody had to finish fourth and I did. Well I think thats the way it is. I gave it all. It was good day a hard day. Could have been better with a medal," a dejected Bindra, who had finished seventh, said later.
Participating in his fifth Olympics, the 33-year-old got off to a good start with scores of 29.9 and 30.2 in the first two series placing him in the top three.
He fell to the fourth spot after a relatively poor 21.1 in the third series with a total score of 81.2. But luck favoured Bindra in the fourth series as he climbed to second with 21.5 as the other shooters in the top four also faltered.
However, Bindra seemed to let the pressure get to him as his performance started to go downhill from there. The former World Champion registered progressively poorer scores of 20.8, 20.2 in the next two series.
A brilliant series of high 10s saw him go up to second after 11 shots and third after 12.
He maintained the position till the 14th shot but a couple of poor shots saw him score 20.1 in what would eventually be his final series and tied at fourth with Ukranian Serhiy Kulish after the 16th shot.
In the shoot-off that followed, Bindra could manage only a 10.0 while the Ukranian shot a brilliant 10.5 to move ahead, thus relegating the Indian to the fourth place.
The same event witnessed a heartbreak for Gagan Narang who finished a lowly 23rd in the qualification round. He could only manage 621.7 and crashed out of the event which gave him a bronze medal in the London Games.
Trap shooters Manavjit Singh Sandhu and Kynan Chenai also brought bad news by failing to enter the semi-finals after finishing 16th and 19th.
Sandhu, in his fourth Olympics, lost out after scoring a cumulative total of 115 while Chenai scored one less to be out of the fray on the second day of qualifications.
However, from the shooting range, Bindra came agonisingly close to another medal
Archer Laxmirani bowed out of the women's individual event, beaten 101-108 by Slovakian Alexandra Longova. The Indian trailed for the very beginning of the contest and lost three of the four rounds, eventually going down 25-27, 26-28, 26-26, 24-27.
In hockey, it was a familiar scene where India failed to remain in control in the final moments. Christopher Ruhr deflected the ball from close range in the 60th minute as Germany earned a crucial win in a Pool B match that India deserved a point.
Niklas Wellen scored in the 18th minute to give the two-time defending champions the lead before Rupinder Pal Singh (23rd) brought India level with his third goal in two matches.
In the women's hockey Pool B action, the Indian women's hoc key team was outplayed 0-3 by higher-ranked Britain..
The difference in class and quality between the two teams was clearly on display as world No.7 Britain scored through Giselle Ansley (25th minute), Nicola White (27th) and Alexandra Danson (33rd).
It was India's first loss in Pool B after they drew the opening gam e against Japan 2-2.
There was more disappointment in store for Indian fans in the swimming pool as Shivani Kataria and Sajan Prakash were knocked out in the opening rounds of their respective categories, ending India's campaign in the discipline.
Shivani finished a disappointing 41st to miss the race to the quarter-finals after clocking 2:09:30 minutes in the women's 200m freestyle heats.
The 18-year-old completed the first 50 metres in 29.28 seconds before taking 1:01.36 minutes to reach 100m. She then posted a time of 1:34.95 minutes to reach 150m and eventually completed it in 2:09:30 minutes to finish second in the heat.
Meanwhile, in the men's 200m butterfly event, Prakash clocked 1:59:37 to finish fourth in his heat and 28th overall to bow out of the competition.
The Kerala swimmer got off to a poor start as he failed to feature in the top three even after the completion of the first 100 metres.
Hungarians Tamas Kenderesi and Laszlo Cseh topped the list clocking 1:54:73 and 1:55:14 minutes respectively while South African Chad Guy Bertrand Le Clos took 1:55:57 minutes to finish third.