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Cowdrey's father, Ernest Arthur Cowdrey, played for the Surrey County Cricket Club Second XI and Berkshire County Cricket Club in the Minor Counties, but lacked the talent to enter first-class cricket and his father made him join a bank. Ernest Cowdrey had been born in Calcutta, moved to India to run a tea plantation and played the 1926-27 MCC touring team for the Madras Europeans XI and top scored with 48. His mother, Molly Cowdrey (nee Taylor), played tennis and hockey. Michael Colin Cowdrey was born on his father's tea plantation at Ootacamund, Madras Presidency, although his birthplace was usually misrecorded as Bangalore 100 miles to the north.

I scored 114 in the first innings and 97 in the second. I will not claim that the first innings was a particularly good one, as it took me almost seven hours. But neither would I pretend that it was not immensely satisfying. I took ball after ball, blow after blow on that improvised body-shield but was able to stand firm...The second innings was the best I ever played. From the firm foundations of real confidence I was able to get after the bowling and repay Hall, particularly, for some of the anguish he had caused me. I had one glorious hour against him...I hooked him twice in a row and reduced him to the kind of despair which, but a fortnight earlier, had been exclusively mine.  After the poor tour of Australia the previous year a revamped England team was taken to the Caribbean under the management of the forthright Walter Robins. Cowdrey was roped in to open the innings with Geoff Pullar as May thought he was the best player of fast bowling. Even though it was not to Cowdrey's liking he made 491 runs (54.55) and two centuries. England won the Second Test by 256 runs despite play being held up by a riot, but May suffered an internal injury and had to go to hospital every morning before play. May soldiered on, but Cowdrey knew he would soon be in charge and was so affected by nerves before the Third Test that he "would have given anything not to have played". To face the fast bowlers he wore rubber padding sewn into his shirt and recovered to make 114 and 97 despite Wes Hall taking 7/69 in England's first innings of 277, no one else making over 30. May had to fly home for treatment (and was unfit to play for 18 months) so Cowdrey took charge in the Fourth Test, winning the toss and top scoring with 65 in England's 295 as Hall took 6/90. The West Indies overtook this with 402, but Ted Dexter (110) and Raman Subba Row (100) saved the match. In the Fifth Test Brian Statham flew home to his sick son, but Cowdrey won the toss and again chose to bat, top scoring with 119 in England's 393.  Trailing 1-0 the West Indies needed a win to even the series and Gerry Alexander declared at 338/8 to force a result. Cowdrey was out for a duck and England were 148/6 before they were saved by M.J.K. Smith (96) and Jim Parks (101). Cowdrey declared at 350/7 leaving the West Indies 406 to win in 52 overs and their 209/5 gave England their first series win in the West Indies. Even so, Robins publicly upbraided Cowdrey for not making an earlier declaration to make an exciting finish.
Colin Cowdrey