[1][2] In major tournaments of the time he was an all-comers finalist in the men's doubles at the 1896 Wimbledon Championships partnering with his twin brother Charles Gladstone Allen where they lost to Reggie Doherty and Harold Nisbet.

In 1891 he won his first title at the Boulogne International, Boulogne-sur-Mer, France against Charles Gladstone Allen.

In February 1913 he won his final title at the San Remo International tournament in Italy.

Hunter Bird Allen, the Rector of Colmworth Parish,[13] and Adelaide Mary Gladstone.

[15] It was Hunter Bird who taught Charles and Roy how to play tennis which proved very successful for both of them.