29.10.1999 Rushden & Diamonds FC - Scunthorpe United 2:0 (0:0)
30.10.1999 Aldershot Town - Hednesford Town 1:1 (0:0)
Bath City FC - 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 FC 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 - AFC 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 FC - Yeovil Town 4:2 (1:1)
Rotherham United - Worthing FC 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)
Entscheidungsspiele
08.11.1999 Hednesford Town - Aldershot Town 1:2 (1:0)
09.11.1999 AFC 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) n.V.
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) n.V.
Plymouth Argyle - Brentford FC 2:1 (0:0, 1:1) n.V.
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)
FA Cup
FA Cup