Proudfoot’s association with the O’s began in 1905 when he was signed by manager Sam Ormerod to assist in the club’s first ever season in the Football League. He featured in thirty-two matches that season, with a solitary goal coming in a 3-1 win away to non-league Barking in the second round qualifying of the FA Cup on 28th October 1905.
The half back left for Chelsea during the summer of 1906 and would later play for clubs including Manchester United and Stockport County prior to the outbreak of the First World War. Four years after the conclusion of the conflict, Proudfoot returned to Orient, taking on the role of first team manager in April 1922.
He received a six month suspension from the Football Association in 1928 due to financial irregularities and left the club a year later. However, Proudfoot was reappointed as manager in June 1930, this time staying for just ten months; a spell that is best remembered for the O’s two Football League fixtures played at Wembley (a 3-0 win over Brentford on 22nd November 1930, followed by a 3-1 win over Southend United fourteen days later) and the severe financial difficulties that plagued the club at the time.
He returned for a third and final spell as manager in May 1935, staying until January 1939 and taking his total time in charge to over ten years. Proudfoot remains one of just three men to manage the O’s on a permanent basis on more than one occasion; he is joined on that list by Alec Stock and Jimmy Bloomfield.
