With their immediate target of 214 to avoid the follow-on still some 89 runs away with five wickets in hand, the tourists will look to wicketkeeper-batsman Niroshan Dickwella (25 not out) and new batsman Dilruwan Perera to defy the home side.
The West Indies enjoyed immediate success on the third morning but were then frustrated by the defiance of the fifth-wicket pair until Chandimal's error of judgement.
Taking on the responsibility to repair the considerable damage done to the innings late on the second day and in the third over of the morning when Kemar Roach bowled Roshen Silva, the Sri Lankan captain played positively and dominated a 78-run stand with Dickwella.
Despite continuing assistance from the pitch for the faster bowlers who so unsettled the opposition's top-order, Chandimal and Dickwella saw off the early threat of Roach and Shannon Gabriel.
It prompted the introduction of support seamers Jason Holder and Miguel Cummins, although they failed to have any impact with the Sri Lankan pair growing in confidence and working towards rebuilding the innings from the depths of 43 for four.
Holder finally summoned his lone specialist spinner, Devendra Bishoo, into the attack but it was the return of Gabriel for the last over before the break which brought about the potentially critical breakthrough.
Chandimal, well set and looking good on 44, immediately went after a short, wide delivery and miscued an attempted cut to offer a simple catch to Roston Chase at backward point, his third of the innings.
Brief scores: Sri Lanka 125-5 (D. Chandimal 44; S. Gabriel 2-30, K. Roach 2-34)