Roach played for Trinidad, but before having any great success at first-class level, he was chosen to tour England with a West Indies team in 1928 and scored over 1,000 runs.

When England played in the West Indies in 1930, he recorded his ground-breaking centuries but had intermittent success at Test level afterwards.

Roach was born in Port of Spain, Trinidad,[1] and attended St Mary's College, for whom he played football.

Already judged a leading batsman in Trinidad, other factors cited in his favour included his fielding, given that West Indian teams had been inconsistent in that discipline, and an ability to bowl.

[9] That December, he passed fifty for the first time in first-class matches, when he scored 84 runs for a combined Trinidad and Guiana team.

[8] Even so, he was chosen in the touring party; previews again suggested his fielding and ability to bowl played a part in his selection.

However, all three Test matches were lost by an innings and the poor overall results led commentators to judge the team unsuccessful.

The review of the tour in Wisden Cricketers' Almanack suggested: "Everybody was compelled to realise that the playing of Test Matches between England and West Indies was a mistake".

[13] The Wisden report singled out Roach as a success, and the best of the batsmen who had not toured England before: "Possessed of strong defence and a nice variety of stroke—especially on the off-side—he created a distinctly favourable impression, and he added to his abilities as a run-getter the further qualifications of being a brilliant fieldsman—especially at cover point.

[5][16] He was fourth in the West Indian Test batting averages, but only one other player, Joe Small, reached fifty in the series, and he only did so once.

[5] In his history of West Indies cricket, Michael Manley describes Roach's innings as "dashing" but containing an element of luck which contrasted with the safe play of Headley.

[22] Inter-island politics meant that selectors tended to pick players from the island hosting the Test.

[27] A report in the Sporting Chronicle, a Trinidad newspaper, in April 1931 suggested, without elaboration, that he "was not himself" during the tour, which accounted for his poor form.

[8] His poor form led some critics to call for his exclusion from the West Indies team;[29] he failed in a trial match in early 1933, but was picked to tour England during the 1933 season.

[8] The West Indies team did not perform as well as expected, and lost the Test series 2–0, and their batting was generally unsuccessful.

[5][16] The Wisden report stated: "If not nearly so sound as Headley, Roach was easily the best man in the team to watch, his batting on many occasions being brilliant to a degree.

[30] A review in a Trinidad newspaper suggested that Roach was the "best stroke maker" in England during the 1933 season, but he was undependable when his side faced adverse circumstances.

[1] During the Second World War, he played several non-first-class matches in England for a team styled a "West Indies XI".

In summing up his career, the historian Bridgette Lawrence wrote that his "style took him to the heights and depths of batting".

[36] Michael Manley described Roach as "swashbuckling",[40] playing risky but attractive shots outside off stump.

[5] George John, his former coach, believed that he was more effective on the back foot, and sometimes failed to move his feet when batting, but that his ability to deflect the ball by the movements of his wrist was unsurpassed in the whole world.