He played part-time for Clapton Orient, in the Southern League before being sold to Aston Villa for £300 (2012: £27,000) in March 1906. At the time the fee was undisclosed even to the player. Villa signed Kingaby for the football maximum wage of £4 a week but after two months were unimpressed with his ability. Villa was not willing to lose the £300 by allowing a free transfer. They offered to sell Herbert 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, so he joined Fulham back in the Southern League.
He rejoined Clapton Orient at the start of the 1910-11 season. That year the Football League and the Southern League agreed mutual recognition of each other's retain-and-transfer system. Villa now disclosed that Kingaby was still on their retained players' list and demanded £350. This prevented a move to Croydon Common but he eventually joined Peterborough City.
Kingaby had brought legal proceedings against Villa for preventing him from playing. 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.
- The Manchester Guardian, FOOTBALL PROFESSIONAL'S LAWSUIT; 27 March 1912
- David McArdle, LLB PhD, The Football League's player registration scheme and the Kingaby case Archived 1 March 2010 at the Wayback Machine., accessed 16 December 2012
- Matthew Taylor, ‘Sutcliffe, Charles Edward (1864–1939)’, Oxford Dictionary of National Biography, Oxford University Press, 2004
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