(Associate Members) competition results from 1999/2000
A full listing of matches played in the competition throughout the season
| Southern Section 2nd Round |
| Tuesday, 11th January 2000 |
| Bournemouth (LD2) | 1 | Brighton & Hove Albion (LD3) | 0 | 4,325 |
| after extra time, 90 minutes 0-0, Bournemouth won on golden goal rule |
| Exeter City (LD3) | 2 | Swansea City (LD3) | 0 | 964 |
| Northampton Town (LD3) | 0 | Bristol Rovers (LD2) | 0 | 2,443 |
| after extra time, 90 minutes 0-0, Bristol Rovers won 5-3 on penalties |
| Oxford United (LD2) | 1 | Wycombe Wanderers (LD2) | 1 | 1,798 |
| after extra time, 90 minutes 1-1, Oxford United won 5-3 on penalties |
| Peterborough United (LD3) | 0 | Brentford (LD2) | 1 | 2,430 |
| Plymouth Argyle (LD3) | 0 | Torquay United (LD3) | 1 | 3,124 |
| Wednesday, 12th January 2000 |
| Bristol City (LD2) | 3 | Cheltenham Town (LD3) | 1 | 4,123 |
| Tuesday, 18th January 2000 |
| Barnet (LD3) | 1 | Reading (LD2) | 2 | 1,109 |
| after extra time, 90 minutes 1-1, Reading won on golden goal rule |
| Northern Section 2nd Round |
| Saturday, 8th January 2000 |
| Lincoln City (LD3) | 1 | Scunthorpe United (LD2) | 2 | 3,617 |
| Monday, 10th January 2000 |
| Preston North End (LD2) | 1 | Hartlepool United (LD3) | 2 | 3,635 |
| Tuesday, 11th January 2000 |
| Hull City (LD3) | 2 | Chester City (LD3) | 0 | 1,680 |
| Mansfield Town (LD3) | 0 | Blackpool (LD2) | 1 | 1,844 |
| Rochdale (LD3) | 3 | Macclesfield Town (LD3) | 2 | 1,123 |
| after extra time, 90 minutes 2-2, Rochdale won on golden goal rule |
| Rotherham United (LD3) | 1 | Chesterfield (LD2) | 4 | 1,997 |
| Tuesday, 18th January 2000 |
| Oldham Athletic (LD2) | 0 | Stoke City (LD2) | 1 | 4,682 |
| after extra time, 90 minutes 0-0, Stoke City won on golden goal rule |
| Tuesday, 25th January 2000 |
| Carlisle United (LD3) | 2 | Wigan Athletic (LD2) | 1 | 1,321 |
| Southern Section 1st Round |
| Tuesday, 7th December 1999 |
| 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 |
| Wednesday, 8th December 1999 |
| Reading (LD2) | 1 | Leyton Orient (LD3) | 0 | 1,561 |
| Tuesday, 11th January 2000 |
| Cambridge United (LD2) | 1 | Barnet (LD3) | 2 | 1,556 |
| after extra time, 90 minutes 1-1, Barnet won on golden goal rule |
| Northern Section 1st Round |
| Tuesday, 7th December 1999 |
| 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, Mansfield Town won on golden goal rule |
| 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, Stoke City won on golden goal rule |
| Wigan Athletic (LD2) | 2 | Burnley (LD2) | 1 | 2,085 |
| after extra time, 90 minutes 1-1, Wigan Athletic won on golden goal rule |
| York City (LD3) | 0 | Hull City (LD3) | 1 | 1,005 |
