Departing the club during the summer were Steve Potts, Paul Kitson, Shaka Hislop, Gary Charles and Craig Forrest. On a restricted budget, Roeder signed replacements on free transfers: joining the Hammers were defender Gary Breen, striker Youseff Sofiane and midfielder Edouard Cisse. The team made a bad start, and after losing 4–0 at Newcastle on the opening day they did not win a game until late September when Di Canio scored twice in a 3–2 victory at Chelsea.

They laboured in the League Cup at Chesterfield, winning the tie on penalties, and went out in the next round with a dismal 1–0 home defeat against Oldham Athletic. Only five points were gained from the next nine games and by the end of December the side was in bottom place. Injuries to strikers Di Canio and Kanoute in this period added to the plight and forced Roeder to purchase the experienced striker Les Ferdinand.

The FA Cup saw the Hammers struggle to beat Nottingham Forest 3–2 at home, after which they faced a daunting tie at Manchester United. The 9,000 fans who travelled were badly let down as the Hammers slumped to a 6–0 defeat. Finally in late January West Ham won their first home league game when beating Blackburn Rovers 2–1. Despite further home wins against Tottenham and Sunderland, the pressure of avoiding relegation was intense. Following the 1–0 victory against Middlesbrough manager Roeder collapsed and was rushed to hospital with a brain tumour. He underwent surgery and later recovered but would not take part in any further club matters that season. Club legend Trevor Brooking then agreed to be in charge for the final three games. There were 1–0 victories over Manchester City and Chelsea, but following the 2–2 draw at Birmingham City the club were relegated. The fans were left puzzled as to how a team with so many star names could end up facing life in the Championship.