Second seed Somdev Devvarman and qualifier Yuki Bhambri advanced to the second round of the $50,000 ATP Challenger event with contrasting wins in Charlottesville.
The bonus amount, a 177% increase on the previous season's payout, will be distributed to players based on performance at the nine ATP 1000 tournaments, which rank just below the four Grand Slams in prestige.
Jannik Sinner returns to the Australian Open targeting a third straight title as the Italian seeks to impose a level of supremacy reminiscent of Novak Djokovic's stranglehold on the year's opening Grand Slam.
Indian players enjoyed a good day on the ATP Challenger tour as Yuki Bhambri reached the singles semifinals of the Traralgon event in Australia while Somdev Devvarman and Saketh Myneni reached the quarter-finals of the Charlottesville event in the United States.
Djokovic to face World number 204 Valentin Vacherot next.
Sumit Nagal registered a straight-sets win over Argentine qualifier Nicolas Kicker.
India's Sanam Singh lost to Peter Polanski for the second time in two months and crashed out of the ATP Knoxville Challenger event in the United States.
India youngster Saketh Myneni clinched his maiden ATP Challenger level singles title after getting the better of Aleksandr Nedovyesov of Kazakhstan in a hard-fought three-set match at the Indore Open on Sunday.
His previous best was 97 in February, which he had attained after winning the Chennai Open, an ATP Challenger series event.
The 23-year-old Davis Cupper rallied to beat qualifier Fred Hemmes Jr.
Top seed Somdev Devvarman won his match against Jordi Samper Montana of Spain via a walkover to set up a semi-final clash with his Indian compatriot Yuki Bhambri in the $50,000 ATP Challenger Tennis tournament in Chennai on Thursday.
Kyrgios beats Sabalenka in 'Battle of the Sexes' showdown
The 45-year-old Bopanna's final appearance on the Tour came at the Paris Masters, where he partnered Kazakhstan's Alexander Bublik, losing in the opening round earlier this week.
In the doubles draw, Indian pair Siddhant Banthia and Parikshit Somani beat compatriots Sai Karteek Reddy Ganta and Vishnu Vardhan 6-3, 3-6, 10-7 to book their spot in the quarter-finals.
Yuki Bhambri and his American partner Robert Galloway lost to fourth seeded combine of Francisco Cabral from Portugal and Lucas Miedler from Austria in the final.
Rajeshwaran shown the door at Mumbai Open
Sinner's retirement and world number one Alcaraz's withdrawal due to an ankle injury blows the draw wide open, with Djokovic in the hunt for a record-extending fifth title in Shanghai.
But the big question that keeps striking the mind is, if Indian tennis system can actually claim this win as its own. The answer is: partially.
Novak Djokovic felt unaffected by his recent losses to the top two players in the world, Carlos Alcaraz and Jannik Sinner, saying that while it is not ideal to lose big matches to the top talent regularly
Defending champion Jannik Sinner defeated Daniel Altmaier to avenge a loss two years ago at the French Open as he marched into the third round of the Shanghai Masters with a 6-3, 6-3 victory over the German.
Sumit Nagal, who recently became the first Indian to beat a seeded player in a Grand Slam tournament, will spearhead the Indian challenge in the men's singles competition of the Chennai Open ATP Challenger 100 tournament beginning on Sunday.
The Indian jumped six places following his runner-up finish at the Perugia ATP Challenger tournament on Sunday.
He also overtook his career-best 65-season win tally of 2023 with this win.
Alexander Zverev is convinced there was a defect in the electronic line calling system during his Madrid Open win
Jannik Sinner beat defending champion and Spanish second seed Carlos Alcaraz to win his first Wimbledon title.
Top seed and defending champion Jannik Sinner, playing on his 24th birthday, ended French qualifier Terence Atmane's dream run at the Cincinnati Open with a 7-6(4), 6-2 win on Saturday to reach the final of the US Open tune-up event.
Hady Habib is the first man representing Lebanon to win a singles main draw match at a Grand Slam in the professional era.
Already assured of a spot in the top 10 on Monday, the 23-year-old Jack Draper hoped to make his first foray into a Masters 1000 final a triumphant one when he meets Dane Holger Rune at Indian Wells on Sunday.
Carlos Alcaraz heads to the US Open in his now-familiar role as chief challenger to defending champion Jannik Sinner and the Spaniard will be driven this year by the twin pursuit of Grand Slam glory and the World No. 1 ranking.
'I guess only the top players' images matter. I guess only the independent tribunal's opinion on the top players is taken as sound and right.'
The top-seeded Indian pair of Yuki Bhambri and Saketh Myneni rallied from a set down to beat Christopher Rungkat and Akira Santillan and win the Bangkok Open title, their sixth together on the ATP Challenger Tour, in Nonthaburi, Thailand, Saturday.
Jannik and Carlos are the favourites at Flushing Meadows, but don't write these men off!
Sumit Nagal won the Heilbronner Neckarcup ATP Challenger event beating Alexander Ritschard of Switzerland
Rohan Bopanna teamed up with Belgium's Sander Gille to enter the quarterfinals of the ATP 250 Boss Open in Stuttgart
Factbox on Italy's Jannik Sinner, who beat Germany's Alexander Zverev 6-3, 7-6(4), 6-3 in the Australian Open final
Novak Djokovic became the oldest man to reach the quarter-finals at all four Grand Slams in a single season.
Sumit Nagal attains career-high ATP ranking of 68
With Bopanna's defeat, India's challenge has ended in the elite clay-court tournament.
Sumit Nagal staged a grand recovery to get the better of Jason Jung of Chinese Taipei 3-6, 6-2, 6-0 and book his place in the quarter-finals of the Chennai Open ATP Challenger in Chennai on Thursday.
Nagal is coming off a title triumph during the Heilbronn Challenger last week, which happens to be his second Challenger title this season after the Chennai Challenger in February.