During the 1988–89 English football season, Brentford competed in the Football League Third Division. The gruelling 63-match season is best remembered for the Bees' run to the sixth round of the FA Cup. Brentford narrowly failed to qualify for the play-offs, but the club's final placing of 7th was its highest in the league pyramid since the 1964–65 season.

After a disappointing end to what was a positive first full season in charge, Brentford manager Steve Perryman identified that his principle starting XI would be complete with a creative winger and a reliable goalscoring forward. Perryman broke the Bees' incoming transfer record in July 1988, after spending £77,500 on Sheffield United forward Richard Cadette. Perryman brought experienced winger Neil Smillie back to Griffin Park, 11 years after Smillie had initially played for the Bees on loan. Also arriving at Griffin Park was goalkeeper Tony Parks from Tottenham Hotspur for a £60,000 fee and replaced Gary Phillips, who joined Reading for £25,000. On the eve of the season, right back Roger Joseph, who had been named in the 1987–88 Third Division PFA Team of the Year, joined Wimbledon for a new club record outgoing transfer fee of £150,000.

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