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| Country | England Scotland Wales |
The1999–2000 FA Cup qualifying rounds opened the119th season of competition inEngland for 'The Football Association Challenge Cup' (FA Cup), the world's oldestassociation football singleknockout competition. A total of 579 clubs participated in the competition afterManchester United, who were the winnersthe previous season, decided not enter.
The large number of clubs entering the tournament meant that the competition started with preliminary and four qualifying knockouts for thesenon-League teams. The 32 winning teams from Fourth qualifying round progressed to theFirst round proper, whereLeague teams tiered at Levels 3 and 4 entered the competition.
| Round | Start date | Leagues entering at this round | New entries this round | Winners from previous round | Number of fixtures |
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| Preliminary round | 21 August 1999 | Isthmian League Northern Premier League Southern League (except Premier divisions) | 394 | none | 197 |
| Combined Counties League Eastern Counties League Essex Senior League Hellenic League Kent League Midland Alliance North West Counties League Northern Counties East League Northern League South Western Football League Spartan South Midlands League Sussex County League United Counties League Wessex League Western League | |||||
| First qualifying round | 4 September 1999 | none | 5 | 197 | 101 |
| Second qualifying round | 18 September 1999 | Isthmian League Northern Premier League Southern Football League (Premier divisions) | 67 | 101 | 84 |
| Third qualifying round | 2 October 1999 | none | none | 84 | 42 |
| Fourth qualifying round | 16 October 1999 | Football Conference | 22 | 42 | 32 |
Matches were played on weekend of Saturday 21 August 1999. A total of 394 clubs took part in this stage of the competition, 88 clubs from the four divisions at Level 7 of English football and 306 clubs from fifteen lower level leagues.
Matches were played on weekend of 4 September 1999. A total of 202 clubs took part in this stage of the competition, including the 197 winners from the preliminary round and five clubs, who get a bye to this round:
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Matches were played on weekend of 18 September 1999. A total of 168 clubs took part in this stage of the competition, including the 101 winners from the first qualifying round and 67Level 6 clubs, from Premier divisions of theIsthmian League,Northern Premier League andSouthern Football League, entering at this stage.
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Matches were played on weekend of 2 October 1999. A total of 84 clubs took part, all having progressed from the second qualifying round.
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Matches were played on weekend of Saturday 16 October 1999. A total of 64 clubs took part, 42 having progressed from the third qualifying round and 22 clubs fromFootball Conference, formingLevel 5 of English football, entering at this stage. The round featuredBurgess Hill Town andHorsham YMCA from theSussex County Football League,Crook Town from theNorthern Football League andLymington & New Milton from theWessex Football League still in the competition, being the lowest ranked clubs in this round.
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See1999–2000 FA Cup for details of the rounds from the first round Proper onwards.