The 1999–2000 Football League Trophy, known as the Auto Windscreens Shield for sponsorship reasons, was the 19th staging of the Football League Trophy, a knock-out competition for English football clubs in Second and Third Division. The winners were Stoke City who beat Bristol City 2–1 in the final.
| Auto Windscreens Shield | |
|---|---|
| Tournament details | |
| Country |  England Wales |
| Teams | 48 |
| Defending champions | Wigan Athletic |
| Final positions | |
| Champions | Stoke City |
| Runner-up | Bristol City |
| Tournament statistics | |
| Matches played | 49 |
The competition began on 7 December 1999 and ended with the final on 16 April 2000 at the Wembley Stadium.
In the first round, there were two sections: North and South. In the following rounds each section gradually eliminates teams in knock-out fashion until each has a winning finalist. At this point, the two winning finalists face each other in the combined final to determine the winners of the Football League Trophy.
First round
Southern Section
The teams that given byes to the second round are Bristol City, Bournemouth, Bristol Rovers, Wycombe Wanderers, Brentford, Peterborough United, Exeter City and Plymouth Argyle.
| Date | Home team | Score | Away team | Attendance |
|---|---|---|---|---|
| 7 December | Brighton & Hove Albion | 1 – 0 | Millwall | 2,407 |
| 7 December | Gillingham | 0 – 3 | Torquay United | 2,718 |
| 7 December | Northampton Town | 1 – 0 | Cardiff City | 2,431 |
| 7 December | Oxford United | 2 – 0 | Luton Town | 1,220 |
| 7 December | Southend United | 0 – 1 | Cheltenham Town | 1,227 |
| 7 December | Swansea City | 3 – 1 | Colchester United | 1,222 |
| 8 December | Reading | 1 – 0 | Leyton Orient | 1,561 |
| 11 January | Cambridge United | 1 – 2 | Barnet | 1,556 |
Second round
Southern Section
| Date | Home team | Score | Away team | Attendance |
|---|---|---|---|---|
| 11 January | Bournemouth | 1 – 0 | Brighton & Hove Albion | 4,325 |
| 11 January | Exeter City | 2 – 0 | Swansea City | 964 |
| 11 January | Northampton Town | 0 – 0 | Bristol Rovers | 2,443 |
| Bristol Rovers won 5 – 3 on penalties | ||||
| 11 January | Oxford United | 1 – 1 | Wycombe Wanderers | 1,798 |
| Oxford United won 5 – 3 on penalties | ||||
| 11 January | Peterborough United | 0 – 1 | Brentford | 2,430 |
| 11 January | Plymouth Argyle | 0 – 1 | Torquay United | 3,124 |
| 12 January | Bristol City | 3 – 1 | Cheltenham Town | 4,123 |
| 18 January | Barnet | 0 – 1 | Reading | 1,109 |
Quarter-final
Southern Section
| Date | Home team | Score | Away team | Attendance |
|---|---|---|---|---|
| 24 January | Bristol Rovers | 1 – 2 | Reading | 4,948 |
| 25 January | Brentford | 2 – 0 | Oxford United | 2,942 |
| 25 January | Bristol City | 1 – 1 | Bournemouth | 4,291 |
| Bristol City won 4 – 1 on penalties | ||||
| 25 January | Exeter City | 1 – 0 | Torquay United | 2,599 |
Semi-final
Southern Section
| Date | Home team | Score | Away team | Attendance |
|---|---|---|---|---|
| 15 February | Bristol City | 4 – 0 | Reading | 8,733 |
| 15 February | Exeter City | 3 – 2 | Brentford | 2,392 |
Area finals
Northern Area final
| Rochdale | 1 – 3 | Stoke City |
|---|---|---|
Holt  86' | Hansson 4' Thorne 21', 27' |
| Stoke City | 1 – 0 | Rochdale |
|---|---|---|
| Thorne 86' |
Stoke City beat Rochdale 4–1 on aggregate.
Southern Area final
| Bristol City | 4 – 0 | Exeter City |
|---|---|---|
| Thorpe 4' Beadle 63' Murray 68' Burnell 75' |
| Exeter City | 1 – 1 | Bristol City |
|---|---|---|
| Speakman 30' | Beadle 65' |
Bristol City beat Exeter City 5–1 on aggregate.
Final
| Bristol City | 1 – 2 | Stoke City |
|---|---|---|
| Holland 74' | Match Report | Kavanagh 32' Thorne 82' |
     Bristol City |    Stoke City |
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MATCH RULES
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