F.A. Cup competition results from 1999/2000
A full listing of matches played in the competition throughout the season
| 5th Round |
| Saturday, 29th January 2000 |
| Cambridge United (LD2) | 1 | Bolton Wanderers (LD1) | 3 | 7,523 |
| Coventry City (PREM) | 2 | Charlton Athletic (LD1) | 3 | 23,400 |
| Everton (PREM) | 2 | Preston North End (LD2) | 0 | 37,486 |
| Fulham (LD1) | 1 | Tranmere Rovers (LD1) | 2 | 13,859 |
| Gillingham (LD2) | 3 | Sheffield Wednesday (PREM) | 1 | 10,130 |
| Sunday, 30th January 2000 |
| Aston Villa (PREM) | 3 | Leeds United (PREM) | 2 | 30,026 |
| Chelsea (PREM) | 2 | Leicester City (PREM) | 1 | 30,141 |
| Monday, 31st January 2000 |
| Blackburn Rovers (LD1) | 1 | Newcastle United (PREM) | 2 | 29,946 |
| 4th Round |
| Saturday, 8th January 2000 |
| Aston Villa (PREM) | 1 | Southampton (PREM) | 0 | 25,025 |
| Charlton Athletic (LD1) | 1 | Queens Park Rangers (LD1) | 0 | 16,798 |
| Coventry City (PREM) | 3 | Burnley (LD2) | 0 | 22,774 |
| Everton (PREM) | 2 | Birmingham City (LD1) | 0 | 25,405 |
| Fulham (LD1) | 3 | Wimbledon (PREM) | 0 | 16,877 |
| Grimsby Town (LD1) | 0 | Bolton Wanderers (LD1) | 2 | 4,270 |
| Newcastle United (PREM) | 4 | Sheffield United (LD1) | 1 | 36,220 |
| Plymouth Argyle (LD3) | 0 | Preston North End (LD2) | 3 | 10,824 |
| Sheffield Wednesday (PREM) | 1 | Wolverhampton Wanderers (LD1) | 1 | 18,506 |
| Tranmere Rovers (LD1) | 1 | Sunderland (PREM) | 0 | 15,469 |
| Wrexham (LD2) | 1 | Cambridge United (LD2) | 2 | 7,186 |
| Sunday, 9th January 2000 |
| Arsenal (PREM) | 0 | Leicester City (PREM) | 0 | 35,710 |
| Manchester City (LD1) | 2 | Leeds United (PREM) | 5 | 29,240 |
| Monday, 10th January 2000 |
| Liverpool (PREM) | 0 | Blackburn Rovers (LD1) | 1 | 32,839 |
| Tuesday, 11th January 2000 |
| Gillingham (LD2) | 3 | Bradford City (PREM) | 1 | 7,091 |
| Wednesday, 19th January 2000 |
| Chelsea (PREM) | 2 | Nottingham Forest (LD1) | 0 | 30,125 |
| 3rd Round Replay |
| Tuesday, 21st December 1999 |
| Everton (PREM) | 1 | Exeter City (LD3) | 0 | 16,869 |
| Luton Town (LD2) | 0 | Fulham (LD1) | 3 | 8,170 |
| Plymouth Argyle (LD3) | 1 | Reading (LD2) | 0 | 8,965 |
| Rushden & Diamonds (CONF) | 1 | Sheffield United (LD1) | 1 | 6,010 |
| after extra time, 90 minutes 0-0, Sheffield United won 6-5 on penalties |
| Torquay United (LD3) | 2 | Queens Park Rangers (LD1) | 3 | 5,232 |
| Wednesday, 22nd December 1999 |
| Blackburn Rovers (LD1) | 2 | West Bromwich Albion (LD1) | 0 | 11,766 |
| after extra time, 90 minutes 0-0 |
| Leicester City (PREM) | 2 | Hereford United (CONF) | 1 | 12,157 |
| after extra time, 90 minutes 1-1 |
| Newcastle United (PREM) | 6 | Tottenham Hotspur (PREM) | 1 | 35,415 |
| Saturday, 8th January 2000 |
| Gillingham (LD2) | 2 | Walsall (LD1) | 1 | 6,538 |
| after extra time, 90 minutes 1-1 |
| Oxford United (LD2) | 1 | Nottingham Forest (LD1) | 3 | 7,191 |
| 3rd Round |
| Friday, 10th December 1999 |
| Cambridge United (LD2) | 2 | Crystal Palace (LD1) | 0 | 5,631 |
| Nottingham Forest (LD1) | 1 | Oxford United (LD2) | 1 | 8,079 |
| Saturday, 11th December 1999 |
| Aston Villa (PREM) | 2 | Darlington (LD3) | 1 | 22,101 |
| Darlington reinstated in 'lucky loser' draw due to Manchester United's non-participation |
| Charlton Athletic (LD1) | 2 | Swindon Town (LD1) | 1 | 10,939 |
| Crewe Alexandra (LD1) | 1 | Bradford City (PREM) | 2 | 6,571 |
| Derby County (PREM) | 0 | Burnley (LD2) | 1 | 23,400 |
| Exeter City (LD3) | 0 | Everton (PREM) | 0 | 6,045 |
| Fulham (LD1) | 2 | Luton Town (LD2) | 2 | 8,251 |
| Grimsby Town (LD1) | 3 | Stockport County (LD1) | 2 | 3,400 |
| Hereford United (CONF) | 0 | Leicester City (PREM) | 0 | 7,795 |
| Hull City (LD3) | 1 | Chelsea (PREM) | 6 | 10,279 |
| Norwich City (LD1) | 1 | Coventry City (PREM) | 3 | 15,702 |
| Preston North End (LD2) | 2 | Oldham Athletic (LD2) | 1 | 9,940 |
| Queens Park Rangers (LD1) | 1 | Torquay United (LD3) | 1 | 8,843 |
| Reading (LD2) | 1 | Plymouth Argyle (LD3) | 1 | 8,536 |
| Sheffield Wednesday (PREM) | 1 | Bristol City (LD2) | 0 | 11,644 |
| Sunderland (PREM) | 1 | Portsmouth (LD1) | 0 | 26,535 |
| Tranmere Rovers (LD1) | 1 | West Ham United (PREM) | 0 | 13,629 |
| Walsall (LD1) | 1 | Gillingham (LD2) | 1 | 4,314 |
| Watford (PREM) | 0 | Birmingham City (LD1) | 1 | 8,144 |
| West Bromwich Albion (LD1) | 2 | Blackburn Rovers (LD1) | 2 | 10,609 |
| Wigan Athletic (LD2) | 0 | Wolverhampton Wanderers (LD1) | 1 | 10,531 |
| Wimbledon (PREM) | 1 | Barnsley (LD1) | 0 | 4,505 |
| Wrexham (LD2) | 2 | Middlesbrough (PREM) | 1 | 11,755 |
| Sunday, 12th December 1999 |
| Chester City (LD3) | 1 | Manchester City (LD1) | 4 | 5,469 |
| Huddersfield Town (LD1) | 0 | Liverpool (PREM) | 2 | 23,678 |
| Leeds United (PREM) | 2 | Port Vale (LD1) | 0 | 11,912 |
| Sheffield United (LD1) | 1 | Rushden & Diamonds (CONF) | 1 | 10,104 |
| Tottenham Hotspur (PREM) | 1 | Newcastle United (PREM) | 1 | 33,116 |
| Monday, 13th December 1999 |
| Arsenal (PREM) | 3 | Blackpool (LD2) | 1 | 34,143 |
| Ipswich Town (LD1) | 0 | Southampton (PREM) | 1 | 14,383 |
| Tuesday, 21st December 1999 |
| Bolton Wanderers (LD1) | 1 | Cardiff City (LD2) | 0 | 5,734 |
| 2nd Round Replay |
| Tuesday, 30th November 1999 |
| Brighton & Hove Albion (LD3) | 1 | Plymouth Argyle (LD3) | 2 | 5,710 |
| Cardiff City (LD2) | 1 | Bury (LD2) | 0 | 4,511 |
| after extra time, 90 minutes 0-0 |
| Enfield (N/L) | 0 | Preston North End (LD2) | 3 | 1,808 |
| Halifax Town (LD3) | 0 | Reading (LD2) | 1 | 2,156 |
| Hull City (LD3) | 3 | Hayes (CONF) | 2 | 7,000 |
| after extra time, 90 minutes 1-1 |
| Lincoln City (LD3) | 0 | Luton Town (LD2) | 1 | 3,822 |
| Oxford United (LD2) | 2 | Shrewsbury Town (LD3) | 1 | 4,096 |
| after extra time, 90 minutes 1-1 |
| Rushden & Diamonds (CONF) | 3 | Ilkeston (N/L) | 0 | 4,226 |
| Wigan Athletic (LD2) | 2 | Wycombe Wanderers (LD2) | 1 | 3,967 |
| 2nd Round |
| Friday, 19th November 1999 |
| Luton Town (LD2) | 2 | Lincoln City (LD3) | 2 | 4,291 |
| Saturday, 20th November 1999 |
| Blackpool (LD2) | 2 | Hendon (N/L) | 0 | 2,975 |
| Bournemouth (LD2) | 0 | Bristol City (LD2) | 2 | 5,223 |
| Burnley (LD2) | 2 | Rotherham United (LD3) | 0 | 8,110 |
| Bury (LD2) | 0 | Cardiff City (LD2) | 0 | 2,603 |
| Cambridge United (LD2) | 1 | Bamber Bridge (N/L) | 0 | 3,303 |
| Exeter City (LD3) | 2 | Aldershot Town (N/L) | 0 | 4,151 |
| Gillingham (LD2) | 3 | Darlington (LD3) | 1 | 5,168 |
| Hayes (CONF) | 2 | Hull City (LD3) | 2 | 2,749 |
| Ilkeston (N/L) | 1 | Rushden & Diamonds (CONF) | 1 | 2,737 |
| Oldham Athletic (LD2) | 1 | Swansea City (LD3) | 0 | 4,332 |
| Plymouth Argyle (LD3) | 0 | Brighton & Hove Albion (LD3) | 0 | 7,414 |
| Preston North End (LD2) | 0 | Enfield (N/L) | 0 | 11,566 |
| Reading (LD2) | 1 | Halifax Town (LD3) | 1 | 5,918 |
| Shrewsbury Town (LD3) | 2 | Oxford United (LD2) | 2 | 3,357 |
| Stalybridge Celtic (N/L) | 1 | Chester City (LD3) | 2 | 3,312 |
| Wrexham (LD2) | 2 | Rochdale (LD3) | 1 | 3,408 |
| Wycombe Wanderers (LD2) | 2 | Wigan Athletic (LD2) | 2 | 2,992 |
| Sunday, 21st November 1999 |
| Forest Green Rovers (CONF) | 0 | Torquay United (LD3) | 3 | 2,962 |
| Hereford United (CONF) | 1 | Hartlepool United (LD3) | 0 | 4,914 |
| 1st Round Replay |
| Monday, 8th November 1999 |
| Hednesford Town (CONF) | 1 | Aldershot Town (N/L) | 2 | 1,719 |
| Tuesday, 9th November 1999 |
| Bournemouth (LD2) | 4 | Notts. County (LD2) | 2 | 4,026 |
| Brighton & Hove Albion (LD3) | 3 | Peterborough United (LD3) | 0 | 5,612 |
| Bury (LD2) | 2 | Tamworth (N/L) | 1 | 2,531 |
| after extra time, 90 minutes 1-1 |
| Cardiff City (LD2) | 3 | Leyton Orient (LD3) | 1 | 3,095 |
| Chester City (LD3) | 3 | Whyteleafe (N/L) | 1 | 2,183 |
| Gillingham (LD2) | 3 | Cheltenham Town (LD3) | 2 | 4,352 |
| Hull City (LD3) | 4 | Macclesfield Town (LD3) | 0 | 4,844 |
| Plymouth Argyle (LD3) | 2 | Brentford (LD2) | 1 | 5,409 |
| after extra time, 90 minutes 1-1 |
| Rochdale (LD3) | 3 | Burton Albion (N/L) | 0 | 2,633 |
| Stalybridge Celtic (N/L) | 3 | Merthyr Tydfil (N/L) | 1 | 1,399 |
| Wednesday, 10th November 1999 |
| Kettering Town (CONF) | 0 | Wrexham (LD2) | 2 | 2,611 |
| Tuesday, 16th November 1999 |
| Oxford City (N/L) | 0 | Wycombe Wanderers (LD2) | 1 | 4,004 |
| 1st Round |
| Friday, 29th October 1999 |
| Rushden & Diamonds (CONF) | 2 | Scunthorpe United (LD2) | 0 | 4,112 |
| Saturday, 30th October 1999 |
| Aldershot Town (N/L) | 1 | Hednesford Town (CONF) | 1 | 3,269 |
| Bath City (N/L) | 0 | Hendon (N/L) | 2 | 1,690 |
| Blackpool (LD2) | 2 | Stoke City (LD2) | 0 | 4,721 |
| Brentford (LD2) | 2 | Plymouth Argyle (LD3) | 2 | 4,287 |
| Bristol City (LD2) | 3 | Mansfield Town (LD3) | 2 | 5,411 |
| Burton Albion (N/L) | 0 | Rochdale (LD3) | 0 | 3,103 |
| Cambridge City (N/L) | 0 | Wigan Athletic (LD2) | 2 | 4,024 |
| Cambridge United (LD2) | 1 | Gateshead (N/L) | 0 | 2,970 |
| Cheltenham Town (LD3) | 1 | Gillingham (LD2) | 1 | 3,188 |
| Chesterfield (LD2) | 1 | Enfield (N/L) | 2 | 2,506 |
| Darlington (LD3) | 2 | Southport (CONF) | 1 | 4,313 |
| Doncaster Rovers (CONF) | 0 | Halifax Town (LD3) | 2 | 5,588 |
| Exeter City (LD3) | 2 | Eastwood Town (N/L) | 1 | 2,441 |
| Forest Green Rovers (CONF) | 6 | Guiseley (N/L) | 0 | 1,047 |
| Hayes (CONF) | 2 | Runcorn FC Halton (N/L) | 1 | 890 |
| Hereford United (CONF) | 1 | York City (LD3) | 0 | 2,787 |
| Ilkeston (N/L) | 2 | Carlisle United (LD3) | 1 | 1,748 |
| Leyton Orient (LD3) | 1 | Cardiff City (LD2) | 1 | 3,109 |
| Lincoln City (LD3) | 1 | Welling United (CONF) | 0 | 2,766 |
| Luton Town (LD2) | 4 | Kingstonian (CONF) | 2 | 4,682 |
| Macclesfield Town (LD3) | 0 | Hull City (LD3) | 0 | 2,401 |
| Notts. County (LD2) | 1 | Bournemouth (LD2) | 1 | 3,674 |
| Oldham Athletic (LD2) | 4 | Chelmsford City (N/L) | 0 | 4,392 |
| Oxford United (LD2) | 3 | Morecambe (CONF) | 2 | 3,504 |
| Peterborough United (LD3) | 1 | Brighton & Hove Albion (LD3) | 1 | 7,260 |
| Reading (LD2) | 4 | Yeovil Town (CONF) | 2 | 8,032 |
| Rotherham United (LD3) | 3 | Worthing (N/L) | 0 | 3,716 |
| Shrewsbury Town (LD3) | 2 | Northampton Town (LD3) | 1 | 2,584 |
| St. Albans City (N/L) | 0 | Bamber Bridge (N/L) | 2 | 1,127 |
| Swansea City (LD3) | 2 | Colchester United (LD2) | 1 | 3,622 |
| Tamworth (N/L) | 2 | Bury (LD2) | 2 | 2,743 |
| Torquay United (LD3) | 1 | Southend United (LD3) | 0 | 2,520 |
| Whyteleafe (N/L) | 0 | Chester City (LD3) | 0 | 2,164 |
| Wrexham (LD2) | 1 | Kettering Town (CONF) | 1 | 2,701 |
| Wycombe Wanderers (LD2) | 1 | Oxford City (N/L) | 1 | 2,963 |
| Sunday, 31st October 1999 |
| Barnet (LD3) | 0 | Burnley (LD2) | 1 | 2,563 |
| Bristol Rovers (LD2) | 0 | Preston North End (LD2) | 1 | 6,145 |
| Hartlepool United (LD3) | 1 | Millwall (LD2) | 0 | 2,847 |
| Tuesday, 2nd November 1999 |
| Merthyr Tydfil (N/L) | 2 | Stalybridge Celtic (N/L) | 2 | 871 |
