Early Career
Headley made his Jamaica debut against Lord Tennyson's XI at Sabina Park on 9 February 1928, in a match won easily by the home team. Batting at number three, his first innings yielded 16 runs, but in the second innings, he scored 71, reaching fifty runs in as many minutes. In the second game against Lord Tennyson's XI which began in Kingston on 18 February, Headley scored his maiden first-class century. Having scored 22 not out after the first day's play, he reached 50 runs by playing very carefully but subsequently played more adventurous shots. He hit the bowling of Alan Hilder for four consecutive fours and twice hit Lord Tennyson for three fours in a row. At one point, thirteen of his scoring shots in a row went for four. He was finally out for 211, the highest score at the time by a West Indian batsman against an English team. After the innings, Tennyson compared Headley to Victor Trumper and Charlie Macartney, batsmen considered among the best who ever played. Headley concluded the series against Tennyson's team with innings of 40 and 71, to give him an aggregate of 409 runs at an average of 81.80. He also took his maiden first class wicket.
Following his success, Headley abandoned his prospective career in dentistry. Although some critics expected his selection for the West Indies tour of England in 1928, Headley was not chosen. While West Indies played their inaugural Test series during that tour, Headley continued to play for St Catherine's. He had another opportunity against English opposition in 1929, when a team led by Julien Cahn arrived to play two first-class games. Jamaica's distance from other Caribbean islands made it difficult for their cricketers to gain good-quality playing experience, so the frequent visits by English sides were important to the development of Jamaican cricket. These tours also served to build Headley's reputation. In the first match, Headley played a slow, defensive innings of 57, but he did not reach fifty in his other three innings. Even so, he was chosen by the Jamaican selectors for a West Indies XI, which included players from other islands, to play Cahn's team in their final tour match. The home side lost the toss and had to bat in very difficult conditions following rain. Headley found the fast bowlers difficult, but survived the period when the pitch was most difficult to bat on before he was out for 44. In the second innings, he attacked from the start and used a wide range of shots to reach 143 before he was run out. In three matches against the tourists, Headley scored 326 runs, averaging 54.33.
A change in the location of his job meant that Headley moved to the Lucas Cricket Club in 1929. He visited America and played some exhibition matches for the Jamaican Athletic Club in New York, scoring a century against a touring team from Bermuda; his parents had moved to America by then, which enabled Headley to combine the cricket with his first visit to his parents in ten years.
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