1971 Kingston, Jamaica
It was the proverbial watershed year for Indian cricket. They beat the mighty West Indies in a Test series, India's maiden triumph over the Caribbeans, and discovered a batting genius in Sunil Gavaskar. The series defining win came in the second Test at Trinidad. Bishan Singh Bedi and EAS Prasanna took seven wickets apiece as India bowled out WI for 214 and then made 352 as Dileep Sardesai (112), Gavaskar (65) and Eknath Solkar (55) chipped in with bat. Charlie Davis was West Indies' pillar (71 n.o. and 74 n.o,) as the hosts set India a target of 124. Gavaskar made an unbeaten 67 as India scored a seven-wicket win and held onto the lead for the remaining three Tests.
1997, Kensington Oval, Barbados
Led by a hundred by Shiv Chanderpaul, West Indies made a 298 in their first innings and India took slender first innings lead (319 all out) as Sachin Tendulkar (92), Rahul Dravid (78) made gritty fifties. Indian pace troika - Venkatesh Prasad, Abey Kuruvilla and Dodda Ganesh - ran through the Windies line-up in the second innings to bowl them out for 140. But their West Indian counterparts - Curtly Ambrose, Ian Bishop and Franklyn Rose - produced an even mightier show as India were skittled for 81 in 35.5 overs.
2002, St John’s, Antigua
The match as such offered little else. It was a morose draw on a pitch flatter than a National Highway. But Anil Kumble gave us a piece of cricketing moment that forever will be remembered. The leg-spinner got hit on the jaw by a Mervyn Dillon bouncer but came out to bowl in the next innings with a bandaged head. He bowled 14 overs on the trot and dismissed Brian Lara. Anil Kumble has always been a synonym with grit.
2011, Wankhede Stadium, Mumbai
Six West Indian top order batsmen went past 50 (Darren Bravo 166, Adrian Barath 62, Kraigg Brathwaite 68, Kirk Edwards 86, Kieron Powell 81 and Marlon Samuel 61) as West Indies posted 590 all out. India replied through a rather unlikely centurion in R Ashwin (103) and made 482. Pragyan Ojha (6/47) and Ashwin (4/34) ensured that India's target will be an attainable 243. But West Indies kept on taking wickets and it boiled down to two runs off last ball for India to win. Ashwin's scamper for second run resulted in him getting run out. Scores were level at 242/9 and the match was drawn.
2013, Kolkata and Mumbai
The cricket was as unremarkable as you'd get anywhere. India strode over West Indies with ease. But that mattered little as cricketing icon Sachin Tendulkar ended his 24-year-long cricketing journey with that series. The much-awaited Tendulkar hundred in his last Test was not there but all other ingredients were there - emotion, tears, a moving farewell speech etc.