During the 1927–28 English football season, Brentford competed in the Football League Third Division South. A season of transition saw the Bees finish in mid-table and score 76 goals, which was at that time the club's best goalscoring tally since joining the Football League in 1920.

Despite a sizeable amount of money in the bank after the previous season's cup exploits and big money sales of Jack Allen, Archie Clark and George Anderson, Brentford manager Harry Curtis elected to add to rather than rebuild his squad for the 1927–28 season, investing in Scottish youngsters John Cairns, Jimmy Drinnan, William Hodge, Alexander Stevenson, Samuel Ward and English teenager Joe Wiggins. Three defeats in the opening 10 matches of the season sent the Bees as high as second place, with summer signing Jack Phillips scoring 9 goals, Herbert Lawson five and Ernie Watkins four. The goals had dried up by mid-October 1927 and Brentford lost 11 of 15 matches in all competitions, sinking to 15th in the table and suffering a club record FA Cup defeat to Manchester United, losing 7–1 after having received a bye to the third round. A 3–2 victory over Walsall at Griffin Park on 5 December (one of just two wins in the midst of the bad run) was witnessed by 2,024, the club record lowest for a home Football League match.

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