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Reading 
  FC Results 1999/2000 Season
  Nationwide Division Two
| Date | Competition | Opposition | Score | Att | Pos | Scorers | 
| Sat July 17 | FRIENDLY | Farnborough (A) | 2-2 | - | - | Brayson (2) | 
| Sat July 24 | FRIENDLY | NEWCASTLE (H) | 2-2 | 16,864 | - | Caskey, Williams | 
| Mon July 26 | FRIENDLY | Basingstoke (A) | 2-1 | - | - | - | 
| Wed July 28 | FRIENDLY | Barnet (A) | 0-0 | - | - | - | 
| Sat July 31 | FRIENDLY | SOUTHAMPTON (H) | 0-3 | 5,000ish | - | - | 
| Mon Aug 2 | FRIENDLY | Woking (A) | 1-3 | - | - | Scott | 
| Sat Aug 7 | League | BRISTOL CITY | 
    2-1 | 13,348 | 6 | Brebner, Crawford | 
| Wed Aug 11 | League Cup 1:1 | PETERBOROUGH | 0-0 | 4,615 | - | - | 
| Sat Aug 14 | League |  Cambridge United | 
    1-3 | 4,600 | 17 | McIntyre | 
| Sat Aug 21 | League |  LUTON TOWN | 
    1-2 | 8,741 | 19 | Williams | 
| Tue Aug 24 | League Cup 1:2 | Peterborough | 2-1 | 4,109 | - | Caskey, Scott | 
| Sat Aug 28 | League | Colchester | 
    2-3 | 3,443 | 21 | Forster, Williams | 
| Wed Sep 1 | League | PRESTON NE | 
    2-2 | 7,628 | 20 | Smith, Scott | 
| Sat Sep 11 | League |  Bournemouth | 
    1-3 | 6,007 | 23 | Caskey | 
| Wed Sep 15 | League Cup 2:1 | Bradford City | 1-1 | 4,961 | - | Caskey | 
| Sat Sep 18 | League |  CHESTERFIELD | 
    1-0 | 6,962 | 19 | Caskey | 
| Wed Sep 22 | League Cup 2:2 | BRADFORD CITY | 2-2 | 6,842 | - | Scott, Hunter | 
| Sat Sep 25 | League |  OLDHAM | 
    1-1 | 7,274 | 18 | Polston | 
| Sat Oct 2 | League |  Wycombe Wanderers  | 
    3-5 | 7,000 | 19 | Forster (2), Caskey | 
| Sat Oct 9 | League |  Stoke City | 
    1-2 | 9,621 | 19 | Forster | 
| Sat Oct 16 | League |  WIGAN | 
    0-2 | 7,708 | 21 | - | 
| Wed Oct 20 | League | BURY | 
    2-0 | 5,393 | 20 | Scott, Williams | 
| Sat Oct 23 | League | Oldham | 
    2-1 | 4,963 | 17 | Gurney, Caskey | 
| Sat Oct 30 | FA Cup 1 | YEOVIL TOWN | 4-2 | 8,032 | - | Bernal, Caskey, Hunter, Williams | 
| Tue Nov 2 | League |  Brentford | 
    1-1 | 6,774 | 16 | Gurney | 
| Sun Nov 7 | League |  OXFORD UNITED | 
    1-2 | 10,101 | 19 | McIntyre | 
| Tue Nov 16 | League | Millwall | 0-5 | 5,202 | 20 | - | 
| Sa Nov 20 | FA Cup 2 | HALIFAX TOWN | 1-1 | 5,918 | - | Caskey | 
| Wed Nov 24 | League |  BURNLEY | 
    0-0 | 6,149 | 20 | - | 
| Sat Nov 27 | League |  SCUNTHORPE | 
    1-1 | 6,142 | 20 | Hunter | 
| Tue Nov 30 | FA Cup 2R |  Halifax Town | 
    1-0 | 2,146 | - | Caskey | 
| Sat Dec 4 | League |  Bristol City | 
    1-3 | 8,946 | 21 | Caskey | 
| Wed Dec 8 | AWS South 1 |  LEYTON ORIENT | 
    1-0 | 1,561 | - | Bernal | 
| Sat Dec 11 | FA Cup 3 | PLYMOUTH | 1-1 | 8,536 | - | McIntyre | 
| Sat Dec 18 | League |  WREXHAM | 
    2-2 | 6,232 | 21 | Grant, Scott | 
| Tue Dec 21 | FA Cup 3R | Plymouth Argyle | 0-1 | - | - | - | 
| Sun Dec 26 | League |  Cardiff City | 
    0-1 | 9,741 | 21 | - | 
| Tue Dec 28 | League |  NOTTS COUNTY | 
    0-0 | 7,703 | 21 | - | 
| Mon Jan 3 2000 | League | Gillingham | 
    2-2 | 7,453 | 21 | Nicholls, Williams | 
| Sat Jan 8 | League |  BLACKPOOL | 
    1-1 | 7,297 | 21 | Caskey | 
| Sat Jan 15 | League | CAMBRIDGE UNITED | 
    0-0 | 6,953 | 21 | - | 
| Tue Jan 18 | AWS South 2 | Barnet | 2-1 | 1,109 | - | Caskey, Scott | 
| Sat Jan 22 | League | Luton Town | 
    1-3 | 6,044 | 22 | Caskey | 
| Mon Jan 24 | AWS South QF |  Bristol Rovers | 
    2-1 | 4,948 | - | Nicholls (2) | 
| Sat Jan 29 | League | COLCHESTER UNITED | 
    2-0 | 7,304 | 20 | Caskey (2) | 
| Sat Feb 5 | League | Preston NE | 
    2-2 | 12,638 | 20 | Forster, Butler | 
| Tue Feb 8 | League | Blackpool | 
    2-0 | 4,291 | 18 | McIntyre, Butler | 
| Sat Feb 12 | League | MILLWALL | 
    2-0 | 11,994 | 17 | Parkinson, Forster | 
| Tue Feb 15 | AWS South SF | Bristol City | 
    0-4 | 8,733 | - | - | 
| Sat Feb 19 | League | Scunthorpe | 
    2-2 | 4,082 | 17 | Caskey, McIntyre | 
| Sat Feb 26 | League |  Chesterfield | 
    0-2 | 2,986 | 18 | - | 
| Sat Mar 4 | League | BOURNEMOUTH | 
    2-0 | 10,551 | 18 | Caskey,Forster | 
| Tue Mar 7 | League |  Oxford United | 
    3-1 | 7,638 | 18 | OG, Hodges, Caskey | 
| Sat Mar 11 | League |  BRENTFORD | 
    1-0 | 11,427 | 16 | A.Williams | 
| Sat Mar 18 | League |  Burnley | 
    0-3 | 14,436 | 17 | - | 
| Wed Mar 22 | League |  BRISTOL ROVERS | 
    2-0 | 11,707 | 15 | Forster, Caskey | 
| Sat Mar 25 | League | CARDIFF CITY | 
    0-1 | 10,044 | 16 | - | 
| Sat Apr 1 | League | Wrexham  | 
    1-0 | 2,613 | 16 | Butler | 
| Tue Apr 4 | League | Bristol Rovers | 
    1-0 | 7,771 | 13 | Caskey | 
| Fri Apr 7 | League | GILLINGHAM | 
    2-2 | 11,064 | 12 | Butler, Caskey | 
| Sat Apr 15 | League |  Notts County  | 
    2-1 | 4,791 | 13 | Forster, Newman | 
| Sat Apr 22 | League | Wigan | 
    0-1 | 5,855 | 13 | - | 
| Mon Apr 24 | League | WYCOMBE WANDERERS | 
    2-1 | 11,834 | 12 | Forster, M.Williams | 
| Sat Apr 29 | League | Bury | 
    1-1 | 3,869 | 12 | Caskey | 
| Sat May 6 | League | STOKE CITY | 1-0 | 13,146 | 10 | Caskey | 
Reading FC 1999-2000 Information