Auto Windscreens Shield 1999-2000 
Winners: Stoke City Runners-up: Bristol City Winners from previous season: Wigan Athletic First round
| Northern section | Carlisle United, Chester City, Chesterfield, Lincoln City, Macclesfield Town, Oldham Athletic, Rochdale and Scunthorpe United given byes to the second round. | | 7 December 1999 | Hartlepool United | 1 | - | 0 | Halifax Town | 1,482 | Victoria Park, Hartlepool | | 7 December 1999 | Mansfield Town (won in sudden death extra time by golden goal) | 2 | - | 1 | Bury | 1,205 | Field Mill, Mansfield (aet) | | 7 December 1999 | Notts County | 0 | - | 1 | Blackpool | 1,167 | Meadow Lane, Nottingham | | 7 December 1999 | Preston North End | 4 | - | 1 | Wrexham | 3,306 | Deepdale, Preston | | 7 December 1999 | Rotherham United | 2 | - | 1 | Shrewsbury Town | 1,166 | Millmoor, Rotherham | | 7 December 1999 | Stoke City (won in sudden death extra time by golden goal) | 3 | - | 2 | Darlington | 3,341 | Victoria Ground, Stoke (aet) | | 7 December 1999 | Wigan Athletic (won in sudden death extra time by golden goal) | 2 | - | 1 | Burnley | 2,085 | JJB Stadium, Wigan (aet) | | 7 December 1999 | York City | 0 | - | 1 | Hull City | 1,005 | Bootham Crescent, York | Southern Section
| AFC Bournemouth, Brentford, Bristol City, Bristol Rovers, Exeter City, Peterborough United, Plymouth Argyle and Wycombe Wanderers given byes to the second round. | | 7 December 1999 | Brighton & Hove Albion | 1 | - | 0 | Millwall | 2,407 | Withdean Stadium, Brighton | | 7 December 1999 | Gillingham | 0 | - | 3 | Torquay United | 2,718 | Priestfield, Gillingham | | 7 December 1999 | Northampton Town | 1 | - | 0 | Cardiff City | 2,431 | Sixfields Stadium, Northampton | | 7 December 1999 | Oxford United | 2 | - | 0 | Luton Town | 1,220 | Manor Ground, Oxford | | 7 December 1999 | Southend United | 0 | - | 1 | Cheltenham Town | 1,227 | Roots Hall, Southend | | 7 December 1999 | Swansea City | 3 | - | 1 | Colchester United | 1,222 | Vetch Field, Swansea | | 8 December 1999 | Reading | 1 | - | 0 | Leyton Orient | 1,561 | Madjeski Stadium, Reading | 11 January 2000 | Cambridge United | 1 | - | 2 | Barnet (won in sudden death extra time by golden goal) | 1,556 | Abbey Stadium, Cambridge (aet) | Second round | Northern section | | 8 January 2000 | Lincoln City | 1 | - | 2 | Scunthorpe United | 3,617 | Sincil Bank, Lincoln | | 10 January 2000 | Preston North End | 1 | - | 2 | Hartlepool United | 3,635 | Deepdale, Preston | | 11 January 2000 | Hull City | 2 | - | 0 | Chester City | 1,680 | Boothferry Park, Kingston-upon-Hull | | 11 January 2000 | Mansfield Town | 0 | - | 1 | Blackpool | 1,844 | Field Mill, Mansfield | | 11 January 2000 | Rochdale (won in sudden death extra time by golden goal) | 3 | - | 2 | Macclesfield Town | 1,123 | Spotland, Rochdale (aet) | | 11 January 2000 | Rotherham United | 1 | - | 4 | Chesterfield | 1,997 | Millmoor, Rotherham | | 18 January 2000 | Oldham Athletic | 0 | - | 1 | Stoke City (won in sudden death extra time by golden goal) | 4,682 | Boundary Park, Oldham | | 25 January 2000 | Carlisle United | 2 | - | 1 | Wigan Athletic | 1,321 | Brunton Park, Carlisle | Southern section | | 11 January 2000 | AFC Bournemouth (won in sudden death extra time by golden goal) | 1 | - | 0 | Brighton & Hove Albion | 4,325 | Dean Court, Bournemouth (aet) | | 11 January 2000 | Exeter City | 2 | - | 0 | Swansea City | 964 | St James's Park, Exeter | | 11 January 2000 | Northampton Town | 0 | - | 0 | Bristol Rovers (won 3-5 on pens.) | 2,443 | Sixfields Stadium, Northampton (aet) | | 11 January 2000 | Oxford United (won 5-3 on pens.) | 1 | - | 1 | Wycombe Wanderers | 1,798 | Manor Ground, Oxford (aet) | | 11 January 2000 | Peterborough United | 0 | - | 1 | Brentford | 2,430 | London Road, Peterborough | | 11 January 2000 | Plymouth Argyle | 0 | - | 1 | Torquay United | 3,124 | Home Park, Plymouth | | 12 January 2000 | Bristol City | 3 | - | 1 | Cheltenham Town | 4,123 | Ashton Gate, Bristol | | 18 January 2000 | Barnet | 1 | - | 2 | Reading (won in sudden death extra time by golden goal) | 1,109 | Underhill Stadium, London (aet) | | Quarter-finals | | Northern section | | 25 January 2000 | Blackpool | 1 | - | 2 | Stoke City | 4,943 | Bloomfield Road, Blackpool | | 25 January 2000 | Rochdale (won 5-4 on pens.) | 0 | - | 0 | Hull City | 1,745 | Spotland, Rochdale (aet) | | 25 January 2000 | Scunthorpe United | 1 | - | 2 | Chesterfield | 2,532 | Glanford Park, Scunthorpe | | 22 February 2000 | Hartlepool United | 1 | - | 2 | Carlisle United | 2,399 | Victoria Park, Hartlepool | Southern section | | 24 January 2000 | Bristol Rovers | 1 | - | 2 | Reading | 4,948 | Memorial Stadium, Bristol | | 25 January 2000 | Brentford | 2 | - | 0 | Oxford United | 2,942 | Griffin Park, London | | 25 January 2000 | Bristol City (won 4-1 on pens.) | 1 | - | 1 | AFC Bournemouth | 4,291 | Ashton Gate, Bristol (aet) | | 25 January 2000 | Exeter City | 1 | - | 0 | Torquay United | 2,599 | St James's Park, Exeter | Semi-Finals | Northern section | | 15 February 2000 | Chesterfield | 0 | - | 1 | Stoke City | 3,825 | Recreation Ground, Chesterfield | | 7 March 2000 | Carlisle United | 0 | - | 1 | Rochdale | 1,792 | Brunton Park, Carlisle | Southern section | | 15 February 2000 | Bristol City | 4 | - | 0 | Reading | 8,733 | Ashton Gate, Bristol | | 15 February 2000 | Exeter City | 3 | - | 2 | Brentford | 2,392 | St James's Park, Exeter | Area Finals | Northern section: 1st leg | | 14 March 2000 | Rochdale | 1 | - | 3 | Stoke City | 4,241 | Spotland, Rochdale | | Southern section: 1st leg | | 29 February 2000 | Bristol City | 4 | - | 0 | Exeter City | 12,742 | Ashton Gate, Bristol | | Northern section: 2nd leg | | 22 March 2000 | Stoke City | 1 | - | 0 | Rochdale | 16,876 | Britannia Stadium, Stoke-on-Trent | | (Stoke City win 4-1 on aggregate) | Southern section: 2nd leg | | 14 March 2000 | Exeter City | 1 | - | 1 | Bristol City | 2,929 | St James's Park, Exeter | (Bristol City win 5-1 on aggregate) | National final | 16 April 2000 | Bristol City | 1 | - | 2 | Stoke City | 75,057 | Wembley Stadium, London |
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