| Wednesday, 22nd September 1999 |
| Worthington League Cup |
| |
2nd Round 2nd Leg |
| |
Blackburn Rovers (LD1) |
3 |
Portsmouth (LD1) |
1 |
7,512 |
|
| Blackburn Rovers won 6-1 on aggregate |
| |
Bristol City (LD2) |
0 |
Nottingham Forest (LD1) |
0 |
8,259 |
|
| Nottingham Forest won 2-1 on aggregate |
| |
Coventry City (PREM) |
3 |
Tranmere Rovers (LD1) |
1 |
12,433 |
|
| Tranmere Rovers won 6-4 on aggregate |
| |
Derby County (PREM) |
3 |
Swansea City (LD3) |
1 |
19,152 |
|
| Derby County won 3-1 on aggregate |
| |
Everton (PREM) |
0 |
Oxford United (LD2) |
1 |
10,006 |
|
| Oxford United won 2-1 on aggregate |
| |
Leicester City (PREM) |
4 |
Crystal Palace (LD1) |
2 |
12,762 |
|
| Leicester City won 7-5 on aggregate |
| |
Reading (LD2) |
2 |
Bradford City (PREM) |
2 |
6,892 |
|
| after extra time, 90 minutes 1-1, aggregate score 3-3, Bradford City won on the away goals rule |
| |
Sheffield Wednesday (PREM) |
3 |
Stoke City (LD2) |
1 |
10,993 |
|
| Sheffield Wednesday won 3-1 on aggregate |
| Tuesday, 21st September 1999 |
| Worthington League Cup |
| |
2nd Round 2nd Leg |
| |
Aston Villa (PREM) |
5 |
Chester City (LD3) |
0 |
22,613 |
|
| Aston Villa won 6-0 on aggregate |
| |
Bolton Wanderers (LD1) |
2 |
Gillingham (LD2) |
0 |
3,673 |
|
| Bolton Wanderers won 6-1 on aggregate |
| |
Bournemouth (LD2) |
0 |
Charlton Athletic (LD1) |
0 |
4,369 |
|
| after extra time, 90 minutes 0-0, aggregate score 0-0, Bournemouth won 3-1 on penalties |
| |
Bristol Rovers (LD2) |
0 |
Birmingham City (LD1) |
1 |
5,456 |
|
| Birmingham City won 3-0 on aggregate |
| |
Fulham (LD1) |
2 |
Norwich City (LD1) |
0 |
5,246 |
|
| Fulham won 6-0 on aggregate |
| |
Ipswich Town (LD1) |
1 |
Crewe Alexandra (LD1) |
1 |
9,689 |
|
| Crewe Alexandra won 3-2 on aggregate |
| |
Leyton Orient (LD3) |
1 |
Grimsby Town (LD1) |
0 |
1,036 |
|
| Grimsby Town won 4-2 on aggregate |
| |
Liverpool (PREM) |
4 |
Hull City (LD3) |
2 |
24,318 |
|
| Liverpool won 9-3 on aggregate |
| |
Middlesbrough (PREM) |
2 |
Chesterfield (LD2) |
1 |
25,602 |
|
| Middlesbrough won 2-1 on aggregate |
| |
Notts. County (LD2) |
2 |
Huddersfield Town (LD1) |
2 |
4,104 |
|
| Huddersfield Town won 4-3 on aggregate |
| |
Preston North End (LD2) |
3 |
Sheffield United (LD1) |
0 |
5,658 |
|
| Preston North End won 3-2 on aggregate |
| |
Southampton (PREM) |
4 |
Manchester City (LD1) |
3 |
10,960 |
|
| after extra time, 90 minutes 3-3, Southampton won 4-3 on aggregate |
| |
Stockport County (LD1) |
3 |
Barnsley (LD1) |
3 |
3,332 |
|
| after extra time, 90 minutes 2-2, aggregate score 4-4, Barnsley won on the away goals rule |
| |
Walsall (LD1) |
0 |
Sunderland (PREM) |
5 |
5,109 |
|
| Sunderland won 8-2 on aggregate |
| |
Wigan Athletic (LD2) |
3 |
Watford (PREM) |
1 |
5,006 |
|
| after extra time, 90 minutes 3-1, aggregate score 3-3, Watford won on the away goals rule |
| |
Wimbledon (PREM) |
3 |
Cardiff City (LD2) |
1 |
2,772 |
|
| Wimbledon won 4-2 on aggregate |
| |
Wycombe Wanderers (LD2) |
3 |
West Bromwich Albion (LD1) |
4 |
5,047 |
|
| after extra time, 90 minutes 2-2, West Bromwich Albion won 5-4 on aggregate |
| Nationwide Conference |
| |
Sutton United |
2 |
Welling United |
3 |
|
|
