His brother Edward was a well known cricketer who played for Barbados, Western Province, Natal, Leicestershire and the Army.

He made his debut in important cricket for Barbados in the 1905–06 Inter-Colonial Tournament in Trinidad aged 17.

Before this 1906 tour he was described as "the baby of the team, good and polished bat"[3] and "a member of the famous cricketing family who should score a fine average.

Thereafter he scored 90 against Scotland, 97 in a minor match against Northumberland and Durham, 63 against Leicestershire, 108 against Nottinghamshire and 67 against Northamptonshire.

Thereafter he was a regular member of the Barbados side and was chosen for the combined West Indies team again the M.C.C.

More big scores came regularly with more centuries against Northumberland, Nottinghamshire, Gloucestershire, Surrey, Glamorgan and Norfolk.

team toured the West Indies in 1925–26 and Challenor was an automatic choice for the representative matches against the tourists.

Although he didn't have great success in the trial matches in 1927–28 he was an automatic choice for the West Indies' initial Test tour of England in 1928.