During the 1899–1900 English football season, Brentford competed in the Southern League Second Division. A Middlesex FA investigation into the club's financial affairs necessitated a change to professional status mid-season, but a forgettable campaign ended with the Bees finishing third-from-bottom.

After a difficult first season in the Southern League Second Division, Brentford's AGM in May 1899 revealed that the club had lost £100 on the previous season, taking the overall debt to £180 (equivalent to £25,600 in 2024).^[1] After a series of meetings, a new committee was elected in July after it was decided that the club would continue to operate on an amateur basis.^[1] On the playing side, only six members of the team that finished the previous season remained at the club – goalkeeper Ben Brown, full back George Turner, half backs 'Nick' Mattocks, Billy Smith and forwards Richard Dailley, Thomas Knapman and Charlie Evans.^[1] Incoming transfers included full back Bert Lane, half back G. Pearce and forwards E. Andrews and John Bayne.^[1]

Brentford won and drew each of the opening two Second Division fixtures, with new forward John Bayne scoring in each, before he and George Turner, both soldiers, departed for service in the Second Boer War with their regiments.^[1] Things went from bad to worse in October when the Middlesex FA opened an enquiry into Brentford's "shamateurism", the results of which saw the club fined £10 and suspended from football for a month beginning 20 November.^[1] Additionally, a number of members of the club's committee were suspended sine die or until 30 April 1900.^[1] A new committee took charge of the club and elected to turn professional.^[1]

Following the resumption of competitive play on 23 December, Brentford showed appalling form, failing to win until late March 1900.^[1] A 13-match winless streak, which stretched back to 23 September, culminated in a 7–0 thrashing at the hands of Grays United on 24 March.^[2] Additionally, a meeting had been called in January to discuss if the club could even continue, but donations of £60 (equivalent to £8,500 in 2024) helped to ensure that the Bees would survive for the immediate future.^[1] Late in the season, professional half backs Frederick Broughton and Ralph McElhaney joined the club and immediately fortunes turned around on the pitch, with Brentford winning four and drawing one of the final six matches of the season to finish in 9th position, two places off the bottom.^[1]

Brentford's goal tally listed first.

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

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No. Pos. Nation Player — GK  ENG S. Andrews — GK  ENG Ben Brown — GK  ENG Louis Hare — GK  ENG S. Marshall — DF  ENG R. Davis — DF  ENG E. Dicks — DF  ENG Herbert Edney — DF  ENG Bert Lane — DF  ENG John Pilgrim — MF  ENG R. Allen — MF  ENG Frederick Broughton — MF  ENG F. Dean — MF  ENG P. Duncan — MF  ENG Billy Green — MF   Hay — MF  ENG Joseph Hood — MF  WAL T. Jones — MF  ENG J. Lucas — MF  ENG Alfred Mattocks — MF  ENG William Mehew

No. Pos. Nation Player — MF  SCO Ralph McElhaney — MF  ENG G. Pearce — MF  ENG Billy Smith — FW  ENG Bert Allen — FW  ENG William Allwright — FW  ENG E. Andrews — FW  ENG Benjamin Asbury — FW   "Bailey" — FW  ENG Frederick Carte — FW  ENG Richard Dailley (c) — FW  ENG B. Edwards — FW   Charlie Evans — FW  ENG M. Granger — FW  ENG Thomas Knapman — FW  ENG J. Read — FW  ENG John Richardson — FW  ENG Harry Thurston — FW  ENG Alfred Townsend — FW  ENG S. Vincent — FW  ENG A. Watt

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Left club during season

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

More information No., Pos. ...

No. Pos. Nation Player — DF  SCO George Turner

No. Pos. Nation Player — FW  SCO John Bayne

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• "Bailey" is an alias
• Source: 100 Years of Brentford^[2]