 Along with approximately 25 other boys, Lee was invited for a trial at Lord's early in 1906, and bowled under the observation of Alfred Atfield and the head groundsman, Tom Hearne. Lee described his first over as "six of the worst balls that anyone can ever have pitched", but as his nerves calmed, he improved, and was eventually selected as one of the five ground staff boys by Hearne. As a ground boy, Lee had numerous tasks; sweeping, dusting and cleaning the seats, preparing nets, marking the pitch, weeding and similar. On a match day, jobs included selling scorecards, operating the score-board or fielding in the practice nets. All of this left little time for the boys to practise their own game. No formal coaching was in place, but Lee was guided by a few different players; England internationals Teddy Wynyard and Albert Trott among them. In the 1909 and 1910 seasons, Lee started to gain some attention from Middlesex County Cricket Club: he scored 39 runs in a match for the Middlesex Colts in 1909, and 60 runs against Reading Cricket Club in 1910. He was making more appearances for the Marylebone Cricket Club (MCC), collecting runs and wickets regularly, but not prolifically. In 1911, when a number of the Middlesex side were missing due to trial matches for England selection, Lee was invited to join the team for two County Championship matches in the south-west, against Somerset and Gloucestershire. Placed at number eleven in Middlesex's batting order, Lee batted once in a rain-affected match against Somerset, remaining four not out, and was not required to bowl. Lee did bowl against Gloucestershire, but remained wicketless from nine overs in the match.
