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Clapton born outside right Herbert “Bert” Kingaby began his football career with West Hampstead in 1899 and first played senior football for Queen’s Park Rangers, for whom he made one Southern League appearance in 1899-1900 possibly as a triallist, before returning to West Hampstead, signing for Clapton Orient in August 1903. When Orient joined The Football League in 1905, Kingaby played in their inaugural League fixture, a 2-1 defeat at Leicester Fosse, Kingaby scoring their first ever Football League goal, and before the season was over he was sold to First Division Aston Villa for £300 in March 1906 after 4 goals in 26 appearances for Orient.
He played 4 times for Aston Villa before the end of the season, peculiarly only in away fixtures, but he didn’t impress. Villa was not willing to lose the £300 by allowing a free transfer. They offered to sell Kingaby back at half price but neither Clapton, nor any other club were interested. Kingaby’s wage was stopped but he was placed on Villa’s retained players’ list effectively preventing him earning a living in the English League before in May he moved on to Southern League Fulham, for whom he scored 3 goals in 37 appearances in 1906-07 as they retained the Southern League Championship.
In May 1907 he transferred to Leyton, where he scored 17 goals in 67 appearances over the following three seasons before a move to  Northamptonshire League Peterborough City in October 1910. After two and a half years with “Posh”, he returned to Southern League action with Croydon Common, for whom he continued to play until peacetime football was suspended due to the onset of the First World War, scoring 9 goals in 42 appearances for The Commoners.
Kingaby was the subject of a famous legal case when, supported by the Players’ Union, he challenged the “retain and transfer” system in March 1912. Charles Sutcliffe helped establish the legality of the League transfer system when he was successfully retained by Aston Villa during the Kingaby case before Justice A.T. Lawrence. Kingaby had brought legal proceedings against Villa for preventing him from playing before his move to Fulham. The Players’ Union funded his legal costs but an erroneous strategy by Kingaby’s Counsel resulted in the suit being dismissed. The Union were almost ruined financially and membership fell drastically.
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