The Hammers were in trouble from the start, losing 4–0 at Southampton and 3–1 at home to Charlton. Tony Cottee had been sold to Everton for a sum in excess of £2 million, making him the most expensive player in British football. New signings inside-forward David Kelly and goalkeeper Alan McKnight found it difficult to settle. Although West Ham slumped to 4–1 league defeats against Arsenal and Luton, their form in the League Cup was far better. Sunderland were beaten 5–1 on aggregate and the next round brought a 5–0 demolition of Derby County. The fourth-round home tie with Liverpool shocked the nation as the Hammers crushed the Reds 4–1, with Paul Ince scoring twice. But as the year ended there had only been three league victories and West Ham were bottom of the table.

The New Year saw more league defeats but there was relief in the cups. In the FA Cup Arsenal and Swindon Town were beaten and in the League Cup the Hammers marched into the semi-final after beating Aston Villa 2–1. Still they struggled in the league, and both cup runs finally ended as first Luton Town won 5–0 on aggregate in the League Cup semi-final and then Norwich went through in the FA Cup, winning the quarter-final 3–1 at Carrow Road.

During April there were four successive home games and only the final one against Millwall brought a victory. Remarkably, the remaining seven games of the campaign brought five wins, but sadly the Hammers were relegated after losing 5–1 on the final day at Liverpool.