England need nine wickets on the final day to take a Test series lead and India will require another famous run chase to go 1-0 up in Chennai after 15 wickets tumbled on Monday.
The tourists bowled India out for 337 at M. A. Chidambaram Stadium after Washington Sundar held them up with an excellent unbeaten 85.
Ashwin made 31 before taking 6-61 as England were bowled out for 178 after the in-form Joe Root - who top scored with 40 - opted against enforcing the follow-on.
India pulled off a big run chase to secure a series win in Australia last month and they will have to repeat those final-day heroics after being set 420 to win on a day which saw Ishant Sharma take his 300th wicket in the longest format.
Jack Leach bowled Rohit Sharma with a peach of a delivery to leave India 39-1 at stumps - 381 runs from their huge target.
England had to be patient for a breakthrough after India resumed on 257-6, Leach ending a seventh-wicket stand of 80 by getting Ashwin for 31 with the new ball - Jos Buttler taking an athletic catch.
Root chose to bat again after a combination of Leach (2-105) and James Anderson (2-46) finished off India's first innings - Ben Stokes taking a sensational slip catch for England's highest Test wicket-taker.
Ashwin generated turn and bounce to get Rory Burns caught by Ajinkya Rahane off the first ball of England's second innings before lunch, and he also saw the back of Dom Sibley (16) following the break.
Ishant snared Dan Lawrence leg before to join the 300 club before Ashwin removed Stokes - caught behind for only seven.
Root, who made a double century in the first innings of his 100th Test, added 40 as England took the lead over 400, with Ollie Pope (28), Buttler (24) and Dom Bess (25) also chipping in.
Ashwin continued to get sharp turn on a deteriorating track as Root kept India in the field in the heat rather than declaring, picking up a 28th five-wicket haul by bowling Jofra Archer and ending the innings when Anderson was caught and bowled.
Leach produced a great delivery to strike Rohit's off stump, but Shubman Gill and Cheteshwar Pujara prevented further damage from being done.
Ashwin delivers, Ishant reaches landmark
Spinner Ashwin bowled 55.1 overs as India were made to toil by a Root-inspired England in the first innings but did not appear to be fatigued as he bowled superbly second time around.
He took advantage of a pitch offering an increasing amount of spin, which should have had Leach and Bess rubbing their hands together. Ishant became the sixth Indian bowler to take 300 Test scalps when Lawrence was his only second-innings victim.
Leach sets England on their way
Leach was given the new ball with Archer as Anderson was overlooked and the left-armer conjured up a perfect delivery to dismiss Rohit, getting one to drift and turn away.
That was the tourists' only breakthrough in 13 overs, but they will be expected to come out firing on the last day.
CG United Super50 Cup final between Scorpions, Pride abandoned due to inclement weather
The CG United Super50 final between the Jamaica Scorpions and the Barbados Pride was abandoned without a ball being bowled due to the inclement weather at the Brian Lara Cricket Academy on Saturday.
Barbados Pride, with six titles plus one shared, were hoping to break a mini drought having last won in 2016-17, while Jamaica, with eight titles plus one shared, had ambitions to get back to the summit as their last title was in the 2022-23 season.
Greaves hits unbeaten ton as West Indies dominate Bangladesh
Justin Greaves hit an unbeaten century – his first red-ball ton – as West Indies ended day two of their first Test against Bangladesh with a commanding 410-run lead.
Greaves resumed alongside Joshua Da Silva with West Indies 250-5 after day one in Antigua, eventually slamming 115 runs off 206 balls faced as the hosts established a dominant position.
His steady knock ensured the Windies recovered nicely after slipping to 261-7 early on, while Kemar Roach hit a career-best 47 through four defiant hours at the crease.
Hasan Mahmud took three day-two wickets for Bangladesh, including that of Roach, as his short delivery angled in to clip the top of middle stump.
Windies skipper Kraigg Brathwaite declared to put Bangladesh at the crease late on, and there was no respite for the tourists against the hosts' four-man pace attack.
Zakir Hasan fell to Jayden Seales for 15, while Mahmudul Hasan Joy edged Alzarri Joseph for five shortly after being dropped, leaving Bangladesh 40-2 at stumps.
Data Debrief: Career-best for Greaves
Greaves' unbeaten 115 marked his first century in Test cricket, surpassing his previous best knock – a score of 33 versus Australia in January – by some distance.
His strike rate of 55.83 on Saturday, while steady, also bettered his effort of 55.00 during that match in Brisbane. Thanks to his efforts, Bangladesh have a real mountain to climb on day three.
Greaves’ maiden century powers Windies to control on day two as Bangladesh reeling at 40-2
West Indies took firm control of their opening Test match against Bangladesh as Justin Greaves’ maiden century piloted the Caribbean side to a mammoth first innings total of 450-9 declared at the Sir Viv Richards Stadium in Antigua on Saturday.
The hosts then restricted Bangladesh to 40-2 at the close of day two, leaving the visitors with a steep challenge ahead as they look to recover from a poor start.
Mominul Haque, not out on 7, and Shahadat Hossain, unbeaten on 10, will resume on Sunday with Bangladesh at 40-2, still trailing by 410 runs.
Greaves, who enjoyed sublime form in the Super50 Cup with three consecutive centuries, continued that rich vein of form with an unbeaten 115 that anchored West Indies’ innings and ensured a daunting total on the board.
The 30-year-old’s knock, which lasted just over six hours, had only four boundaries and was crucial in reviving the innings after a mid-session slump.
Scores: West Indies 450-9 dec; Bangladesh 40-2
West Indies resumed the day at 250-5 with Greaves on 11, and Joshua da Silva, 14, looking to consolidate their position. However, early breakthroughs from Bangladesh’s Hasan Mahmud threatened to derail the West Indies’ momentum.
Mahmud struck in the first session, removing da Silva without addition to his overnight score, and Alzarri Joseph (four), who also fell cheaply to leave West Indies at a precarious 261-7.
At that point, the Bangladesh bowlers seemed poised to bowl the Caribbean side down for a score under 300, but Greaves and veteran pacer Kemar Roach had other ideas.
The two Barbadians countered the pressure with patience, building a partnership of 140 runs for the eighth wicket that pushed West Indies past the 400-run mark.
Roach, who had previously struggled with the bat in Tests, made 47—his highest Test score in his 15-year career. He batted for over four hours, frustrating the Bangladesh bowlers with steady defence and timely strokes.
Together, Roach and Greaves weathered the storm, forcing Bangladesh to toil longer and harder than expected. Greaves, in particular, looked in complete control, while Roach’s composed knock provided vital support.
West Indies then made quick inroads in Bangladesh’s reply and reduced the visitors to 2-21, with both openers back in the pavilion cheaply. Alzarri Joseph was the first to strike, removing Mahmudul Hasan Joy for just five runs before Jayden Seales cleaned up Zakir Hasan for 15.
With Bangladesh struggling at 2-21, it seemed as though West Indies were on the brink of another quick domination as they sought to dismiss the Bangladesh top-order cheaply. However, Mominul Haque and Shahadat Hossain managed to negotiate the remainder of the day without further loss.
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