The 1998–99 season was the 119th season of competitive football in England.
Manchester United overcame close competition from Arsenal and Chelsea to win their fifth Premiership title in seven seasons. They went on to win the treble of the Premiership title, FA Cup and European Cup, an achievement which gained manager Alex Ferguson a knighthood.
Nottingham Forest went down to Division One just one season after winning promotion. They had started the season terribly after manager Dave Bassett was sacked and Dutch striker Pierre van Hooijdonk refused to play after a dispute with the club. Experienced Ron Atkinson was brought in on a temporary contract but could not stave off relegation. Joining Forest in the Premiership drop zone were Blackburn Rovers, who had been Premiership champions just four years earlier, and Charlton Athletic. Southampton avoided relegation on the last day of the season, and their survival also signalled the go-ahead for a new stadium which would be in use for the 2001–02 season.
Sunderland were crowned Division One champions with 105 points, then a record, having lost just three games all season. The two other promotion places were secured by two of the division's least fancied sides – runners-up Bradford City (back in the top division for the first time in 77 years) and playoff winners Watford, who thus won their second successive promotion during Graham Taylor's second spell as manager.