Competitions
Semi-finals
Coventry City 1 -
2 Nottingham Forest
West Ham 3 -
6 Oldham Athletic
Quarter-finals
Tottenham 4 -
5 Nottingham Forest
Coventry City 5 -
0 Sunderland
West Ham 3 -
2 Derby County
Oldham Athletic 4 -
2 Southampton
Round of 16
Tottenham 6 -
2 Tranmere Rovers
Sunderland 7 -
4 Exeter City
Southampton 4 -
2 Swindon Town
3rd Round
Nottingham Forest 5 -
0 Crystal Palace
AFC Bournemouth 1 -
2 Sunderland
Swindon Town 7 -
6 Bolton
West Ham 1 -
0 Aston Villa
Wimbledon 2 -
1 Middlesbrough
2nd Round
Wimbledon 5 -
1 Port Vale
Plymouth Argyle 1 -
8 Arsenal
Blackpool 2 -
2 Barnsley
West Ham 3 -
2 Birmingham
Watford 2 -
3 Bolton
Manchester City 5 -
3 Brentford
Coventry City 4 -
3 Grimsby Town
Tranmere Rovers 2 -
0 Ipswich
Derby County 6 -
2 Cambridge United
Leicester City 4 -
4 Crystal Palace
AFC Bournemouth 1 -
0 Crewe Alexandra
Everton 4 -
2 Leyton Orient
Wigan 2 -
8 Liverpool
Luton Town 11 -
5 Mansfield
Leeds United 2 -
4 Oldham Athletic
Newcastle Utd 5 -
3 Reading
Fulham 1 -
4 Sunderland
Millwall 2 -
1 Stoke City
Scarborough Athletic 4 -
3 Chelsea
Swindon Town 6 -
1 Shrewsbury Town
Wolverhampton 2 -
3 Aston Villa
Bradford City 6 -
6 West Bromwich
Southampton 3 -
0 York City
Stockport County 1 -
2 QPR
Halifax Town 0 -
5 Middlesbrough
Rotherham United 0 -
6 Norwich
Huddersfield 4 -
4 Nottingham Forest
Manchester United 3 -
2 Portsmouth
Southend United 3 -
3 Tottenham
Hereford United 1 -
4 Charlton Athletic
Aldershot Town 0 -
8 Sheffield Wednesday
Blackburn 2 -
4 Exeter City
1st Round
Bury 1 -
2 Stockport County
Chesterfield 2 -
3 Birmingham
Burnley 2 -
3 Blackpool
Reading 5 -
4 Bristol City
Lincoln City 0 -
3 Wolverhampton
Carlisle United 2 -
3 Halifax Town
Leyton Orient 7 -
1 Gillingham
Plymouth Argyle 3 -
2 Cardiff City
Maidstone United 1 -
4 Cambridge United
Southend United 6 -
4 Colchester United
Chester City 0 -
6 Crewe Alexandra
Northampton Town 1 -
3 Mansfield
Tranmere Rovers 5 -
6 Preston North End
Wigan 5 -
0 Wrexham
Bolton 6 -
3 Rochdale
Scunthorpe United 1 -
3 Scarborough Athletic
Hereford United 3 -
1 Torquay United
Port Vale 3 -
1 Walsall
Doncaster Rovers 2 -
3 Huddersfield
Grimsby Town 2 -
1 Hull City
Rotherham United 2 -
1 Sheffield United
Notts County 3 -
4 Shrewsbury Town
Brentford 4 -
1 Brighton
Portsmouth 2 -
1 Bristol Rovers
Aldershot Town 6 -
4 Peterborough United
Oxford United 4 -
5 Fulham
York City 7 -
4 Hartlepool United
Swansea 1 -
4 Exeter City
Littlewoods Challenge Cup
| Winner | |
| Country |  England |
| Date | 21.08.1989 - 29.04.1990 |
| Played | 168 of 168 |
