A big centre-half from Dublin, Harry Leddy had a lengthy spell in Irish football before trying his hand at the game across the Irish Sea. It was at the end of 1913-14 when a Shelbourne player, in a season in which he played left-half for The Irish League against The Scottish League in a 2-1 defeat at Windsor Park, Belfast in October 1913 and aided Shelbourne to the Irish Cup semi-final (where they lost to Glentoran after four games), that Leddy moved to Scottish First Division side, Clyde. After just two appearances for Clyde, Leddy returned to Shelbourne, and played out the Great War with spells at Belfast United, Distillery and Glenavon. In March 1919 he played at right-back in both matches of Distillery’s Co. Antrim Shield win over Belfast Celtic. Leddy moved to Tranmere Rovers, then playing in the Cheshire County League and the Central League. His performances attracted the attentions of Tranmere’s Merseyside neighbours, Everton. Despite the £500 fee he never made The Toffees’ first eleven and after less than a year he was on the move to Division Three (North) Chesterfield for around £1,000, making his debut against Ashington in March 1922.
A natural leader and an imposing presence in the centre of defence, Leddy helped lift The Spireites away from the foot of the League and the dreaded “re-election spots”. He was proving good value for the £9-per-week that Chesterfield were paying him, but the Football League were about to throw a spanner in the works in the form of an £8-per-week maximum wage. Would the club honour their contract with a player or the League’s rules? Leddy agreed to a reduced wage but took Chesterfield to court in order to recoup £99 in lost wages. The case developed into a battle between the Players’ Union (now the Professional Footballers’ Association) and the Football League and was eventually settled in the High Court in the Union and Leddy’s favour. Through all the courtroom shenanigans Leddy maintained a high-level of performance and was Chesterfield’s regular penalty-taker as they finished the 1922-23 season in fourth. In May 1923 Leddy transferred to Grimsby Town after 7 goals in 49 games. Although he captained The Mariners he was unable to settle on the east-coast and flitted in-and-out of the side, often at wing-half. He left Blundell Park in May 1925 after 13 games , returning to his native-Dublin to play for Shamrock Rovers in the Irish Free State League.