During the 1998–99 English football season, West Ham United F.C. competed in the FA Premier League (known as the FA Carling Premiership for sponsorship reasons).

In the 1998-99 season, the Hammers finished fifth in the Premier League, their second-best placing ever in the top-flight, securing UEFA Cup qualification to mark a return to European competitions after 19 years in the wilderness (though the Hammers would have qualified for the UEFA Cup through their third-place finish in 1986 had it not been for the ban on English clubs in European competitions).

New additions to the side for the season were goalkeeper Shaka Hislop, defender Neil Ruddock, Marc Keller and Arsenal goalscoring legend Ian Wright, while mid-season arrivals came in the shape of midfielder Marc-Vivien Foé, defender Scott Minto and striker Paolo Di Canio. During the course of the season, several key players left the club, including veteran defender Tim Breacker, unsettled striker John Hartson (who signed for Wimbledon after being linked with a move to a Manchester United side who won the league title, FA Cup and European Cup that season) and winger Andy Impey. April saw the retirement of defender Richard Hall, who had struggled with injuries since his arrival from Southampton in July 1996.

The season also saw the emergence of highly promising midfielder Joe Cole, who played his first eight league games that campaign and made a further appearance in the FA Cup, though he failed to score.

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