Shimron Hetmyer (139) and Shai Hope (102*) struck brilliant centuries to help West Indies chase down the 288-run target in 47.5 overs with eight wickets remaining, against India in the first ODI in Chennai.
The duo put on a mammoth 218-run stand for the second wicket after the fall of Sunil Ambris in the fifth over. The visitors now lead the three-match series 1-0.
Earlier, after being put into bat, India rode on half-centuries from Shreyas Iyer (70) and Rishabh Pant (71) to reach 287/8 in 50 overs. It was Iyer's third consecutive half-century.
The lack of a specialist fifth bowler hurt India as the combination of debutant Shivam Dube (0/68 in 7.5 overs) and Kedar Jadhav (0/11 in one over) leaked 79 runs in 8.5 overs.
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Hetmyer was unstoppable en route to his fifth ODI century, smashing as many as seven sixes including the one that hit the roof.
Hope gave solid support to Hetmyer and deservingly completed his eighth ODI hundred. Another talented southpaw like Hetmyer, Nicholas Pooran (29 not out off 23), hit back-to-back boundaries to register a memorable win for West Indies.
The second game of the three-match series will be played in Visakhapatnam on Wednesday.
Earlier, Pant struck his maiden half-century to silence his critics as India shrugged off a poor start to post a competitive total.
Iyer, who is emerging as a solid number four, and Pant paired up for a 114-run stand for the fourth wicket after India lost opener K.L. Rahul (6) and skipper Virat Kohli (4) in the seventh over of the innings.
Rohit Sharma (36 off 56) too struggled on a slow surface before Iyer and Pant resurrected the innings with their gritty partnership.
A half-century partnership between Kedar Jadhav (40 off 35) and Ravindra Jadeja (21 off 21), who batted ahead of debutant Shivam Dube, provided the thrust in the slog overs.
Left-arm paceman Sheldon Cottrell (2/46 from 10 overs including 3 maidens), Keemo Paul (2/41) and Alzarri Joseph (2/45) were among the wickets for the visiting team.
(With PTI inputs)