| Tuesday, 7th December 1999 |
| Nationwide League Division One |
| |
Blackburn Rovers |
3 |
Bolton Wanderers |
1 |
|
|
| Nationwide League Division Two |
| |
Chesterfield |
0 |
Bristol City |
2 |
|
|
| Auto Windscreens Shield (Associate Members) |
| |
Northern Section 1st Round |
| |
Hartlepool United (LD3) |
1 |
Halifax Town (LD3) |
0 |
1,482 |
|
| |
Mansfield Town (LD3) |
2 |
Bury (LD2) |
1 |
1,205 |
|
| after extra time, 90 minutes 1-1 |
| |
Notts. County (LD2) |
0 |
Blackpool (LD2) |
1 |
1,167 |
|
| |
Preston North End (LD2) |
4 |
Wrexham (LD2) |
1 |
3,306 |
|
| |
Rotherham United (LD3) |
2 |
Shrewsbury Town (LD3) |
1 |
1,166 |
|
| |
Stoke City (LD2) |
3 |
Darlington (LD3) |
2 |
3,341 |
|
| after extra time, 90 minutes 2-2 |
| |
Wigan Athletic (LD2) |
2 |
Burnley (LD2) |
1 |
2,085 |
|
| after extra time, 90 minutes 1-1 |
| |
York City (LD3) |
0 |
Hull City (LD3) |
1 |
1,005 |
|
| |
Southern Section 1st Round |
| |
Brighton & Hove Albion (LD3) |
1 |
Millwall (LD2) |
0 |
2,407 |
|
| |
Gillingham (LD2) |
0 |
Torquay United (LD3) |
3 |
2,718 |
|
| |
Northampton Town (LD3) |
1 |
Cardiff City (LD2) |
0 |
2,431 |
|
| |
Oxford United (LD2) |
2 |
Luton Town (LD2) |
0 |
1,220 |
|
| |
Southend United (LD3) |
0 |
Cheltenham Town (LD3) |
1 |
1,227 |
|
| |
Swansea City (LD3) |
3 |
Colchester United (LD2) |
1 |
1,222 |
|
| Scottish Division One |
| |
Airdrieonians |
1 |
Greenock Morton |
0 |
|
|
| Scottish Division Three |
| |
Brechin City |
0 |
Berwick Rangers |
3 |
|
|
| |
Forfar Athletic |
1 |
Montrose |
2 |
|
|
