Zenith Data Systems Cup 1989-90 
Champions: Chelsea Runners-up: Middlesbrough Winners from previous season: Nottingham Forest | Northern Section | | First round | | 7 November 1989 | Leeds United | 1 | - | 0 | Blackburn Rovers | 5,070 | Elland Road, Leeds | | 7 November 1989 | Sheffield United | 1 | - | 0 | Wolverhampton Wanderers | 4,926 | Bramall Lane, Sheffield | | 14 November 1989 | Sunderland | 1 | - | 2 | Port Vale | 7,035 | Roker Park, Sunderland | Second round
| | 28 November 1989 | Barnsley | 1 | - | 2 | Leeds United | 6,136 | Oakwell, Barnsley | | 28 November 1989 | Hull City | 1 | - | 2 | Aston Villa | 2,888 | Boothferry Park, Kingston-upon-Hull | | 29 November 1989 | Middlesbrough | 3 | - | 1 | Port Vale | 6,691 | Ayresome Park, Middlesbrough | | 28 November 1989 | Newcastle United | 2 | - | 0 | Oldham Athletic | 6,167 | St James's Park, Newcastle | | 29 November 1989 | Nottingham Forest | 3 | - | 2 | Manchester City | 9,729 | City Ground, Nottingham | | 21 November 1989 | Sheffield Wednesday | 3 | - | 2 | Sheffield United | 30,464 | Hillsborough, Sheffield (aet) | | 28 November 1989 | Stoke City | 2 | - | 1 | Bradford City | 4,616 | Victoria Ground, Stoke | | 29 November 1989 | West Bromwich Albion | 0 | - | 5 | Derby County | 4,880 | The Hawthorns, West Bromwich | Third round
| | 22 December 1989 | Aston Villa | 2 | - | 1 | Nottingham Forest | 6,530 | Villa Park, Birmingham | | 20 December 1989 | Middlesbrough | 4 | - | 1 | Sheffield Wednesday | 8,716 | Ayresome Park, Middlesbrough | | 20 December 1989 | Newcastle United | 3 | - | 2 | Derby County | 6,800 | St James's Park, Newcastle (aet) | | 19 December 1989 | Stoke City | 2 | - | 2 | Leeds United (win 5-4 on pens.) | 5,792 | Victoria Ground, Stoke (aet) | | Semi-final | | 17 January 1990 | Aston Villa | 2 | - | 0 | Leeds United | 17,543 | Villa Park, Birmingham | | 23 January 1990 | Middlesbrough | 1 | - | 0 | Newcastle United | 16,948 | Ayresome Park, Middlesbrough | Final: 1st leg
| | 30 January 1990 | Aston Villa | 1 | - | 2 | Middlesbrough | 16,547 | Villa Park, Birmingham | Final: 2nd leg | | 6 February 1990 | Middlesbrough | 2 | - | 1 | Aston Villa | 20,806 | Ayresome Park, Middlesbrough (aet) | | | (Middlesbrough win 4-2 on aggregate) | | | | | | | | Southern Section | First round | | 8 November 1989 | Oxford United | 2 | - | 3 | Luton Town | 1,754 | Manor Ground, Oxford (aet) | | 29 November 1989 | Coventry City | 1 | - | 3 | Wimbledon | 3,781 | Highfield Road, Coventry (aet) | Second round
| | 28 November 1989 | AFC Bournemouth | 2 | - | 3 | Chelsea | 6,214 | Dean Court, Bournemouth (aet) | | 14 November 1989 | Charlton Athletic | 2 | - | 1 | Leicester City | 1,565 | Selhurst Park, London | | 27 November 1989 | Crystal Palace | 4 | - | 1 | Luton Town | 3,747 | Selhurst Park, London | | 21 November 1989 | Ipswich Town | 4 | - | 1 | Watford | 5,078 | Portman Road, Ipswich | | 29 November 1989 | Norwich City | 5 | - | 0 | Brighton & Hove Albion | 5,704 | Carrow Road, Norwich | | 1 December 1989 | Portsmouth | 0 | - | 1 | Wimbledon | 2,499 | Fratton Park, Portsmouth | | 13 December 1989 | Swindon Town | 2 | - | 1 | Millwall | 3,223 | County Ground, Swindon | | 29 November 1989 | West Ham United | 5 | - | 2 | Plymouth Argyle | 5,409 | Boleyn Ground, London (aet) | | Third round | | 22 December 1989 | Chelsea | 4 | - | 3 | West Ham United | 8,418 | Stamford Bridge, London | | 19 December 1989 | Crystal Palace | 2 | - | 0 | Charlton Athletic | 6,621 | Selhurst Park, London | | 21 December 1989 | Ipswich Town | 3 | - | 1 | Wimbledon | 7,918 | Portman Road, Ipswich | | 24 January 1990 | Swindon Town | 4 | - | 1 | Norwich City | 5,314 | County Ground, Swindon | | Semi-final | | 13 February 1990 | Crystal Palace | 1 | - | 0 | Swindon Town | 6,027 | Selhurst Park, London | | 23 January 1990 | Ipswich Town | 2 | - | 3 | Chelsea | 13,365 | Portman Road, Ipswich | Final: 1st leg
| | 21 February 1990 | Crystal Palace | 0 | - | 2 | Chelsea | 14,839 | Selhurst Park, London | Final: 2nd leg
| | 12 March 1990 | Chelsea | 2 | - | 0 | Crystal Palace | 15,061 | Stamford Bridge, London | | | (Chelsea win 4-0 on aggregate) | | | | | | | | | | | | Final | | 25 March 1990 | Chelsea | 1 | - | 0 | Middlesbrough | 76,369 | Wembley Stadium, London | | | Dorigo (25) | | | | | | |
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