1998/99◄ Sheffield Wednesday Results ►2000/01
Season 1999/00
League & Cup Results
| Game | Date | Opposition | Result | H/A | Venue | Competition | 
| 1 | 07/08/1999 | Liverpool | Lost 1-2 | Home | Hillsborough | Premier League | 
| 2 | 11/08/1999 | Manchester United | Lost 0-4 | Away | Old Trafford | Premier League | 
| 3 | 14/08/1999 | Bradford City | Drew 1-1 | Away | Valley Parade | Premier League | 
| 4 | 21/08/1999 | Tottenham Hotspur | Lost 1-2 | Home | Hillsborough | Premier League | 
| 5 | 25/08/1999 | Derby County | Lost 0-2 | Home | Hillsborough | Premier League | 
| 6 | 28/08/1999 | Southampton | Lost 0-2 | Away | The Dell | Premier League | 
| 7 | 11/09/1999 | Everton | Lost 0-2 | Home | Hillsborough | Premier League | 
| 8 | 14/09/1999 | Stoke City | Drew 0-0 | Away | Britannia Stadium | League Cup 2nd Round 1st Leg | 
| 9 | 19/09/1999 | Newcastle United | Lost 0-8 | Away | St James' Park | Premier League | 
| 10 | 22/09/1999 | Stoke City | Won 3-1 | Home | Hillsborough | League Cup 2nd Round 2nd Leg | 
| Sheffield Wednesday Won 3-1 on aggregate | ||||||
| 11 | 25/09/1999 | Sunderland | Lost 0-1 | Away | Stadium of Light | Premier League | 
| 12 | 02/10/1999 | Wimbledon | Won 5-1 | Home | Hillsborough | Premier League | 
| 13 | 13/10/1999 | Nottingham Forest | Won 4-1 | Home | Hillsborough | League Cup 3rd Round | 
| 14 | 16/10/1999 | Leeds United | Lost 0-2 | Away | Elland Road | Premier League | 
| 15 | 23/10/1999 | Coventry City | Drew 0-0 | Home | Hillsborough | Premier League | 
| 16 | 30/10/1999 | Leicester City | Lost 0-3 | Away | Filbert Street | Premier League | 
| 17 | 06/11/1999 | Watford | Drew 2-2 | Home | Hillsborough | Premier League | 
| 18 | 21/11/1999 | West Ham United | Lost 3-4 | Away | Boleyn Ground | Premier League | 
| 19 | 30/11/1999 | Bolton Wanderers | Lost 0-1 | Away | Reebok Stadium | League Cup 4th Round | 
| 20 | 05/12/1999 | Liverpool | Lost 1-4 | Away | Anfield | Premier League | 
| 21 | 11/12/1999 | Bristol City | Won 1-0 | Home | Hillsborough | FA Cup 3rd Round | 
| 22 | 18/12/1999 | Aston Villa | Lost 1-2 | Away | Villa Park | Premier League | 
| 23 | 26/12/1999 | Middlesbrough | Won 1-0 | Home | Hillsborough | Premier League | 
| 24 | 29/12/1999 | Chelsea | Lost 0-3 | Away | Stamford Bridge | Premier League | 
| 25 | 03/01/2000 | Arsenal | Drew 1-1 | Home | Hillsborough | Premier League | 
| 26 | 08/01/2000 | Wolverhampton Wanderers | Drew 1-1 | Home | Hillsborough | FA Cup 4th Round | 
| 27 | 15/01/2000 | Bradford City | Won 2-0 | Home | Hillsborough | Premier League | 
| 28 | 18/01/2000 | Wolverhampton Wanderers | Drew 0-0 | Away | Molineux | FA Cup 4th Round Replay | 
| Sheffield Wednesday Won 4-3 on Penalties | ||||||
| 29 | 22/01/2000 | Tottenham Hotspur | Won 1-0 | Away | White Hart Lane | Premier League | 
| 30 | 29/01/2000 | Gillingham | Lost 1-3 | Away | Priestfield Stadium | FA Cup 5th Round | 
| 31 | 02/02/2000 | Manchester United | Lost 0-1 | Home | Hillsborough | Premier League | 
| 32 | 05/02/2000 | Derby County | Drew 3-3 | Away | Pride Park | Premier League | 
| 33 | 12/02/2000 | Southampton | Lost 0-1 | Home | Hillsborough | Premier League | 
| 34 | 26/02/2000 | Newcastle United | Lost 0-2 | Home | Hillsborough | Premier League | 
| 35 | 04/03/2000 | Everton | Drew 1-1 | Away | Goodison Park | Premier League | 
| 36 | 11/03/2000 | West Ham United | Won 3-1 | Home | Hillsborough | Premier League | 
| 37 | 18/03/2000 | Watford | Lost 0-1 | Away | Vicarage Road | Premier League | 
| 38 | 25/03/2000 | Middlesbrough | Lost 0-1 | Away | Riverside Stadium | Premier League | 
| 39 | 05/04/2000 | Aston Villa | Lost 0-1 | Home | Hillsborough | Premier League | 
| 40 | 12/04/2000 | Wimbledon | Won 2-0 | Away | Selhurst Park | Premier League | 
| 41 | 15/04/2000 | Chelsea | Won 1-0 | Home | Hillsborough | Premier League | 
| 42 | 22/04/2000 | Sunderland | Lost 0-2 | Home | Hillsborough | Premier League | 
| 43 | 30/04/2000 | Leeds United | Lost 0-3 | Home | Hillsborough | Premier League | 
| 44 | 06/05/2000 | Coventry City | Lost 1-4 | Away | Highfield Road | Premier League | 
| 45 | 09/05/2000 | Arsenal | Drew 3-3 | Away | Highbury | Premier League | 
| 46 | 14/05/2000 | Leicester City | Won 4-0 | Home | Hillsborough | Premier League | 
End of Season Review
| League Record | ||||||||
| Pos | Pld | W | D | L | F | A | GD | Pts | 
| ▼19th | 38 | 8 | 7 | 23 | 38 | 70 | -32 | 31 | 
| ▼Sheffield Wednesday were Relegated to Football League Division 1 | ||||||||
| Click here for final League Standings | ||||||||
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         Cup Record  | 
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| Competition | Round Reached | Knocked Out By | 
| FA Cup | 5th Round | Gillingham | 
| Football League Cup | 4th Round | Bolton Wanderers | 
Manager(s)
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1998/99◄ Sheffield Wednesday Results ►2000/01