Primera ronda
29.10.1999 Rushden & Diamonds - Scunthorpe United 2:0 (0:0)
30.10.1999 Aldershot Town - Hednesford Town 1:1 (0:0)
Bath City - Hendon FC 0:2 (0:0)
Blackpool FC - Stoke City 2:0 (1:0)
Brentford FC - Plymouth Argyle 2:2 (0:1)
Bristol City - Mansfield Town 3:2 (1:1)
Burton Albion - Rochdale AFC 0:0 (0:0)
Cambridge United - Gateshead FC 1:0 (0:0)
Cambridge City - Wigan Athletic 0:2 (0:2)
Cheltenham Town - Gillingham FC 1:1 (0:1)
Chesterfield FC - Enfield FC 1:2 (0:1)
Darlington FC - Southport FC 2:1 (1:0)
Doncaster Rovers - Halifax Town 0:2 (0:0)
Exeter City - Eastwood Town 2:1 (1:0)
Forest Green Rovers - Guiseley AFC 6:0 (4:0)
Hayes FC - Runcorn 2:1 (1:1)
Hereford United - York City 1:0 (0:0)
Ilkeston Town - Carlisle United 2:1 (1:1)
Leyton Orient - Cardiff City 1:1 (0:1)
Lincoln City - Welling United FC 1:0 (1:0)
Luton Town - Kingstonian FC 4:2 (1:1)
Macclesfield Town - Hull City 0:0 (0:0)
Notts County - Bournemouth 1:1 (1:0)
Oldham Athletic - Chelmsford City 4:0 (2:0)
Oxford United - Morecambe FC 3:2 (1:1)
Peterborough United - Brighton & Hove Albion 1:1 (1:1)
Reading - Yeovil Town 4:2 (1:1)
Rotherham United - Worthing 3:0 (1:0)
Shrewsbury Town - Northampton Town 2:1 (1:1)
St. Albans City - Bamber Bridge 0:2 (0:1)
Swansea City - Colchester United 2:1 (0:0)
Tamworth FC - Bury FC 2:2 (1:1)
Torquay United - Southend United 1:0 (0:0)
Whyteleafe - Chester City 0:0 (0:0)
Wrexham AFC - Kettering Town 1:1 (0:0)
Wycombe Wanderers - Oxford City 1:1 (0:0)
31.10.1999 Barnet FC - Burnley FC 0:1 (0:0)
Bristol Rovers - Preston North End 0:1 (0:0)
Hartlepool United - Millwall FC 1:0 (0:0)
02.11.1999 Merthyr Tydfil FC - Stalybridge Celtic 2:2 (0:2)
08.11.1999 Hednesford Town - Aldershot Town 1:2 (1:0)
09.11.1999 Bournemouth - Notts County 4:2 (1:0)
Brighton & Hove Albion - Peterborough United 3:0 (1:0)
Bury FC - Tamworth FC 2:1 (0:1, 1:1) pró.
Cardiff City - Leyton Orient 3:1 (1:1)
Chester City - Whyteleafe 3:1 (1:1)
Gillingham FC - Cheltenham Town 3:2 (2:0)
Hull City - Macclesfield Town 4:0 (3:0)
Oxford City - Wycombe Wanderers 1:1 (1:0, 1:1) pró.
Plymouth Argyle - Brentford FC 2:1 (0:0, 1:1) pró.
Rochdale AFC - Burton Albion 3:0 (1:0)
Stalybridge Celtic - Merthyr Tydfil FC 3:1 (2:1)
10.11.1999 Kettering Town - Wrexham AFC 0:2 (0:2)
16.11.1999 Oxford City - Wycombe Wanderers 0:1 (0:0)
Segunda ronda
19.11.1999 Luton Town - Lincoln City 2:2 (0:1)
20.11.1999 Blackpool FC - Hendon FC 2:0 (0:0)
Bournemouth - Bristol City 0:2 (0:1)
Burnley FC - Rotherham United 2:0 (0:0)
Bury FC - Cardiff City 0:0 (0:0)
Cambridge United - Bamber Bridge 1:0 (0:0)
Exeter City - Aldershot Town 2:0 (2:0)
Gillingham FC - Darlington FC 3:1 (2:0)
Hayes FC - Hull City 2:2 (1:1)
Ilkeston Town - Rushden & Diamonds 1:1 (1:0)
Oldham Athletic - Swansea City 1:0 (1:0)
Plymouth Argyle - Brighton & Hove Albion 0:0 (0:0)
Preston North End - Enfield FC 0:0 (0:0)
Reading - Halifax Town 1:1 (0:0)
Shrewsbury Town - Oxford United 2:2 (1:0)
Stalybridge Celtic - Chester City 1:2 (1:1)
Wrexham AFC - Rochdale AFC 2:1 (1:1)
Wycombe Wanderers - Wigan Athletic 2:2 (1:1)
21.11.1999 Forest Green Rovers - Torquay United 0:3 (0:0)
Hereford United - Hartlepool United 1:0 (0:0)
30.11.1999 Brighton & Hove Albion - Plymouth Argyle 1:2 (0:1)
Cardiff City - Bury FC 1:0 (0:0, 0:0) pró.
Enfield FC - Preston North End 0:3 (0:0)
Halifax Town - Reading 0:1 (0:0)
Hull City - Hayes FC 3:2 (0:0, 1:1) pró.
Lincoln City - Luton Town 0:1 (0:0)
Oxford United - Shrewsbury Town 2:1 (0:1, 1:1) pró.
Rushden & Diamonds - Ilkeston Town 3:0 (2:0)
Wigan Athletic - Wycombe Wanderers 2:1 (1:1)
Tercera ronda
10.12.1999 Cambridge United - Crystal Palace 2:0 (0:0)
Nottingham Forest - Oxford United 1:1 (1:0)
11.12.1999 Aston Villa - Darlington FC 2:1 (1:0)
Charlton Athletic - Swindon Town 2:1 (0:0)
Crewe Alexandra - Bradford City 1:2 (0:0)
Derby County - Burnley FC 0:1 (0:0)
Exeter City - Everton 0:0 (0:0)
Fulham FC - Luton Town 2:2 (2:1)
Grimsby Town - Stockport County 3:2 (1:0)
Hereford United - Leicester City 0:0 (0:0)
Hull City - Chelsea 1:6 (1:2)
Norwich City - Coventry City 1:3 (0:0)
Preston North End - Oldham Athletic 2:1 (1:0)
Queens Park Rangers - Torquay United 1:1 (1:0)
Reading - Plymouth Argyle 1:1 (1:0)
Sheffield Wednesday - Bristol City 1:0 (1:0)
Sunderland - Portsmouth FC 1:0 (1:0)
Tranmere Rovers - West Ham United 1:0 (1:0)
Walsall FC - Gillingham FC 1:1 (0:1)
Watford FC - Birmingham City 0:1 (0:0)
West Bromwich Albion - Blackburn Rovers 2:2 (0:0)
Wigan Athletic - Wolverhampton Wanderers 0:1 (0:0)
Wimbledon FC - Barnsley FC 1:0 (1:0)
Wrexham AFC - Middlesbrough 2:1 (0:1)
12.12.1999 Chester City - Manchester City 1:4 (1:1)
Huddersfield Town - Liverpool 0:2 (0:1)
Leeds United - Port Vale FC 2:0 (0:0)
Sheffield United - Rushden & Diamonds 1:1 (1:1)
Tottenham Hotspur - Newcastle United 1:1 (0:0)
13.12.1999 Arsenal - Blackpool FC 3:1 (1:1)
Ipswich Town - Southampton 0:1 (0:1)
21.12.1999 Bolton Wanderers - Cardiff City 1:0 (1:0)
Everton - Exeter City 1:0 (0:0)
Luton Town - Fulham FC 0:3 (0:0)
Plymouth Argyle - Reading 1:0 (0:0)
Rushden & Diamonds - Sheffield United 5:6 (0:0, 0:0, 1:1) pn.
Torquay United - Queens Park Rangers 2:3 (0:0)
22.12.1999 Blackburn Rovers - West Bromwich Albion 2:0 (0:0, 0:0) pró.
Leicester City - Hereford United 2:1 (0:1, 1:1) pró.
Newcastle United - Tottenham Hotspur 6:1 (3:1)
08.01.2000 Gillingham FC - Walsall FC 2:1 (1:1, 1:1) pró.
Oxford United - Nottingham Forest 1:3 (0:0)
Cuarta Ronda
08.01.2000 Aston Villa - Southampton 1:0 (1:0)
Charlton Athletic - Queens Park Rangers 1:0 (0:0)
Coventry City - Burnley FC 3:0 (1:0)
Everton - Birmingham City 2:0 (0:0)
Fulham FC - Wimbledon FC 3:0 (2:0)
Grimsby Town - Bolton Wanderers 0:2 (0:1)
Newcastle United - Sheffield United 4:1 (1:1)
Plymouth Argyle - Preston North End 0:3 (0:1)
Sheffield Wednesday - Wolverhampton Wanderers 1:1 (1:0)
Tranmere Rovers - Sunderland 1:0 (1:0)
Wrexham AFC - Cambridge United 1:2 (1:1)
09.01.2000 Arsenal - Leicester City 0:0 (0:0)
Manchester City - Leeds United 2:5 (2:3)
10.01.2000 Liverpool - Blackburn Rovers 0:1 (0:0)
11.01.2000 Gillingham FC - Bradford City 3:1 (1:0)
19.01.2000 Chelsea - Nottingham Forest 2:0 (0:0)
18.01.2000 Wolverhampton Wanderers - Sheffield Wednesday 3:4 (0:0, 0:0, 0:0) pn.
19.01.2000 Leicester City - Arsenal 6:5 (0:0, 0:0, 0:0) pn.
Octavos de final
29.01.2000 Cambridge United - Bolton Wanderers 1:3 (1:0)
Coventry City - Charlton Athletic 2:3 (2:2)
Everton - Preston North End 2:0 (0:0)
Fulham FC - Tranmere Rovers 1:2 (1:1)
Gillingham FC - Sheffield Wednesday 3:1 (0:1)
31.01.2000 Blackburn Rovers - Newcastle United 1:2 (1:1)
Aston Villa - Leeds United 3:2 (1:2)
Chelsea - Leicester City 2:1 (1:0)
Cuartos de final
19.02.2000 Bolton Wanderers - Charlton Athletic 1:0 (0:0)
20.02.2000 Chelsea - Gillingham FC 5:0 (1:0)
Everton - Aston Villa 1:2 (1:2)
Tranmere Rovers - Newcastle United 2:3 (1:2)
Semifinales
02.04.2000 Bolton Wanderers - Aston Villa 1:4 (0:0, 0:0, 0:0) pn.
09.04.2000 Newcastle United - Chelsea 1:2 (0:1)
Final
20.05.2000 16:00 Aston Villa - Chelsea 0:1 (0:0)