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Young Indian Grandmaster Rameshbabu Praggnanandhaa let veteran Michal Krasenkow off the hook to lose the second game of the two-game mini-match in the third round of FIDE Chess World Cup in Sochi on Monday.
The experienced Pentala Harikrishna, on the other hand, accepted a draw against lower-rated Constantin Lupulescu of Romania to advance to round four with a 1.5-0.5 margin.
A blunder on the 33rd move cost the 15-year old Praggnanandhaa dear as the 57-year-old Poland player used all his experience to close out a 44-move win.
The duo will battle it out in the tie-break on Tuesday to earn a spot in the fourth round.
Meanwhile, another talented Indian Nihal Sarin's campaign came to an end, as he lost 0.5-1.5 to Dmitry Andreikin of Russia.
Having lost the first game on Sunday, the 17-year-old Sarin needed to win the second to force a tie-breaker. He could only manage a draw in 31 moves against the Russian and bowed out of the competition.
The 35-year-old Harikrishna, the second highest ranked Indian at 21 after Viswanathan Anand, ground out a 46-move draw in the second game after having defeated Lupulescu on Sunday.
In an all-Indian clash, Adhiban Baskaran won the second game in 66 moves against Vidit Gujrathi to level the match 1-1 and send the third-round encounter into a tie-break.