1999–2000 Sheffield Wednesday F.C. season
The 1999–2000 season was Sheffield Wednesday's 133rd season in existence. They competed in the twenty-team Premier League, the top tier of English football. The club finished nineteenth and were relegated from the Premier League for the first time.
Season summary
Barring the opening-day 2-1 home defeat to Liverpool, Sheffield Wednesday were in the bottom three virtually all season long. A very poor start to the season saw the club fail to win any of their first nine league games and an 8–0 hammering at the hands of Newcastle United in Septembersaw most people tip the club as favourites for relegation, and this opinion was further strengthened by their failure to make a substantial improvement as the season went on as they won just once in their first 17 games. The board of directors decided that enough was enough and on 21 March, Danny Wilson's managerial contract was terminated, three days after an appalling 1-0 defeat away to a struggling Watford side who had previously won only once in their previous 20 league games. Wilson's assistant Peter Shreeves took temporary charge, and kept the Owls in contention for survival right up to the penultimate day of the season. A failure to beat Arsenal confirmed their relegation after nine successive seasons of top division football, but they did manage a 3–3 draw at Highbury. Bradford City manager Paul Jewell was then given the uphill task of restoring Premier League football to the club, though the club's mounting debts triggered fears that further struggles would lie ahead.
Final league table
;Results summary;Results by round
Results
Sheffield Wednesday's score comes firstLegend
FA Premier League
FA Cup
| Round | Date | Opponent | Venue | Result | Attendance | Goalscorers |
| R3 | 11 December 1999 | Bristol City | H | 1-0 | 11,644 | Booth |
| R4 | 8 January 2000 | Wolverhampton Wanderers | H | 1-1 | 18,506 | Alexandersson |
| R4R | 18 January 2000 | Wolverhampton Wanderers | A | 25,201 | ||
| R5 | 29 January 2000 | Gillingham | A | 1-3 | 10,130 | Sibon |
League Cup
| Round | Date | Opponent | Venue | Result | Attendance | Goalscorers |
| R2 1st Leg | 14 September 1999 | Stoke City | A | 0-0 | 9,313 | |
| R2 2nd Leg | 22 September 1999 | Stoke City | H | 3-1 | 10,993 | Alexandersson, De Bilde |
| R3 | 13 October 1999 | Nottingham Forest | H | 4-1 | 15,524 | Cresswell, Booth, Sonner, Rudi |
| R4 | 30 November 1999 | Bolton Wanderers | A | 0-1 | 12,543 |