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Sri Lanka require nine West Indies wickets to seal victory in the first Test in Georgetown.
The Windies were 96 for one at stumps on day four at Providence Stadium in their pursuit of a victory target of 437.
They need a further 341 runs to pull off the highest fourth-innings run-chase in Test history, with a draw a much more likely prospect.
West Indies’ second innings got off to a shaky start when Devon Smith was brilliant caught by Thilan Thushara off Chaminda Vaas in the fifth over.
West Indies began the day needing eight runs to avoid the follow-on.
They just managed it, adding 11 to their overnight total before losing their final wicket when Daren Powell edged Thushara to Mahela Jayawardene at second slip.
Sri Lanka then made 240 in their second innings before declaring with seven wickets down.
Michael Vandort was the only Sri Lanka wicket to fall before lunch, caught behind by Denesh Ramdin off the bowling of Chris Gayle for 24.
Opener Malinda Warnapura picked up where he left off in the first innings as the tourists looked to build on their 196-run advantage.He scored his maiden century in the first innings and looked likely to follow it with another until he chased a short, wide delivery from Dwayne Bravo and succeeded only in edging to Ramdin midway through the second session for 62.
Having accumulated patiently before lunch, the tourists relented in the afternoon and tried to counteract the Windies’ defensive approach.
Kumar Sangakkara, who scored 50 in the first innings, signalled his intent to push the scoring along by smashing Bravo for four, but he fell on 21 in the third over after lunch when an attempted flick through mid-on off Bravo took a leading edge found Fidel Edwards at mid-off.
Mahela Jayawardene looked in fine touch, adding 33 before top-edging a pull off Sulieman Benn to Shivnarine Chanderpaul at midwicket.
Jerome Taylor trapped Tillakaratne Dilshan lbw for four shortly before tea to give the hosts some hope.
After the interval, Benn had Vaas caught behind by Ramdin for 13 and then tempted Thushara into lobbing to Taylor at long-off.
Thilan Samaraweera (56 not out) kept the runs ticking over for Sri Lanka, however, and captain Mahela Jayawardene called his team in for a second time, leaving them with more than a day to bowl the Windies out.
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