The West Indies still hold the advantage over India in test matches with a 30-23 record despite their decline as a cricketing powerhouse in the last two decades.
As the two teams head into their 100th test starting Thursday in Port of Spain, AFP Sport looks at the five most memorable encounters between them.
FIRST IMPRESSION, 1948-49
West Indies, led by John Goddard, first toured India in 1948-49 and won the five-match series 1-0 in a run-feast in nearly all the matches.
After three high-scoring draws, West Indies won the fourth test in Chennai with fast bowlers Prior Jones, Gerry Gomez and John Trim sharing 17 of the 20 wickets to fall.
India lost by an innings and 193 runs, after they were made to follow-on in response to 582 following centuries by West Indies openers Allan Rae and Jeffrey Stollmeyer.
West Indies star Everton Weekes, who made a match-winning 90, topped the batting chart in the series with 779 runs, including four hundreds.
KANHAI DOUBLE, 1958-59
Rohan Kanhai smashed a match-winning 256 at Calcutta (now Kolkata) in the third test on the 1958-59 tour as India were routed by an innings and 336 runs.
Basil Butcher and Gary Sobers also contributed with 103 and 106 not out but Kanhai stood out in his best-ever test innings, studded with 42 boundaries, to guide West Indies to a mammoth 614-5 declared.
The bowling, led by Roy Gilchrist and Wes Hall, did the rest as the West Indies bowled out India twice for 124 and 154 to lead the five-match series 2-0. They finally won it 3-0.
SUNNY DAYS, 1971
Sunil Gavaskar made a sparkling debut at Port of Spain in 1971 to play a key role in India's first-ever test win over the West Indies.
Gavaskar, fondly called "Sunny" or the "Little Master", made 65 and then an unbeaten 67, as India won by seven wickets for a 1-0 lead, which the tourists retained to clinch the series.
Dilip Sardesai's 112 in India's first innings of 352 also stood out against a formidable West Indies bowling.
Gavaskar amassed 774 runs at an average of 154.8 in the five matches to kickstart his illustrious test journey.
'SUPER CAT' SHOW, 1975
Clive Lloyd led from the front with his test best of 242 not out at Mumbai's Wankhede Stadium in 1975 to help West Indies clinch a series-deciding fifth match in India.
With the series tied at 2-2, Lloyd's 429-minute stay at the wicket and his 250-run sixth-wicket stand with Deryck Murray powered the tourists to 604-6 declared in the six-day test.
It was the only double ton scored by Lloyd, who was called "Super Cat" for his sharp fielding in the cover area, in his illustrious 110-test career.
India fought back with a first-innings reply of 406, but lost by 201 runs while chasing 404 on the final day of the test.
DRAVID SPECIAL, 2006
Rahul Dravid won many a game for India with his resolute batting including a series-clinching victory in the West Indies in 2006.
After three drawn games, Dravid's India won the final match by 49 runs with the captain scoring 81 and 68 in the first and second innings of a low-scoring game in Kingston.
Dravid stood out with his dogged effort in the match as the visitors scored 200 and 171 against a Brian Lara-led West Indies.
The 1-0 series was Dravid's highlight, along with a series win in England, in his otherwise low-key captaincy stint.