| Tuesday, 12th October 1999 |
| Worthington League Cup |
| |
3rd Round |
| |
Arsenal (PREM) |
2 |
Preston North End (LD2) |
1 |
15,239 |
|
| |
Birmingham City (LD1) |
2 |
Newcastle United (PREM) |
0 |
19,795 |
|
| |
Bradford City (PREM) |
2 |
Barnsley (LD1) |
3 |
8,583 |
|
| |
Tranmere Rovers (LD1) |
2 |
Oxford United (LD2) |
0 |
5,328 |
|
| |
West Bromwich Albion (LD1) |
1 |
Fulham (LD1) |
2 |
10,556 |
|
| |
Wimbledon (PREM) |
3 |
Sunderland (PREM) |
2 |
4,790 |
|
| after extra time, 90 minutes 1-1 |
| CIS Insurance Scottish League Cup |
| |
3rd Round |
| |
Aberdeen (SPL) |
1 |
Falkirk (SCD1) |
1 |
|
|
| after extra time, 90 minutes 0-0, Aberdeen won 5-3 on penalties |
| |
Alloa Athletic (SCD2) |
1 |
Dundee (SPL) |
3 |
|
|
| |
East Fife (SCD3) |
0 |
Heart of Midlothian (SPL) |
2 |
|
|
| |
Inverness Caledonian Thistle (SCD1) |
0 |
Motherwell (SPL) |
1 |
|
|
| |
Kilmarnock (SPL) |
3 |
Hibernian (SPL) |
2 |
|
|
| |
Rangers (SPL) |
1 |
Dunfermline Athletic (SCD1) |
0 |
|
|
| |
St. Johnstone (SPL) |
1 |
Dundee United (SPL) |
2 |
|
|
