| 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 |
