On 15 January 1927 Wakelam gave the first ever running sports commentary on BBC radio. It covered the Rugby International match between England and Wales at Twickenham. England won 11-9. While Wakelam described the run of play, a background voice would call out a number (this referred to a specific area on the pitch). To assist listeners, a picture showing a rugby field divided into numbered squared was published in the Radio Times. It is believed the British phrase "Back to Square One" (meaning to restart something) originates from this practice.
A week after his broadcasting debut on rugby he and C.A. Lewis provided the first sports commentary of a football on British radio. The games, which was Arsenal - Sheffield United, finished as a 1-1 draw. In the same year he covered cricket and Wimbledon. In the mid 1930s he accidentally set fire to his notes while commentating on the tennis but kept going as if nothing had happened.
In June 1938, Wakelam became one of the first sports commentators on BBC television covering the England v Australia second test match at Lord's Cricket Ground in London. Although he commentated on other sports like boxing, his speciality remained rugby union.
Wakelam also covered non-sporting events like Tidworth Tattoo. He also worked as a rugby correspondent for The Morning Post and wrote a number of books including the Harlequin Story (1954) about the history of his old club.
Only a handful of his commentaries using the "squares" system have survived. English journalist, author and cricket commentator, John Arlott called him "a natural talker with a reasonable vocabulary, a good rugby mind and a conscious determination to avoid journalese."