| No. | Date | Home | Score | Away | Competition | Attendance | Notes |
| 1 | 16/7/99 | Cambridge City | 0-4 | Cambridge Utd | Friendly | 1251 | |
| 2 | 20/7/99 | Braintree Town | 3-5 | Cambridge Utd | Friendly | - | |
| 3 | 21/7/99 | Soham Town Rangers | 0-2 | Cambridge Utd | Friendly | - | |
| 4 | 24/7/99 | Cambridge Utd | 0-1 | Bolton Wanderers | Friendly | 2125 | |
| 5 | 28/7/99 | Wisbech Town | 3-2 | Cambridge Utd | Addenbrookes Cup | - | |
| 6 | 31/7/99 | Cambridge Utd | 1-3 | Leyton Orient | Friendly | 1429 | |
| 7 | 3/8/99 | Wroxham | 1-3 | Cambridge Utd | Christopher Bush Memorial Fund | - | |
| 8 | 7/8/99 | AFC Bournemouth | 2-1 | Cambridge Utd | Division 2 | 5552 | |
| 9 | 10/8/99 | Cambridge Utd | 2-2 | Bristol City | Worthington Cup 1st round 1st leg | 2813 | |
| 10 | 14/8/99 | Cambridge Utd | 3-1 | Reading | Division 2 | 4630 | |
| 11 | 18/8/99 | Cambridge Utd | 0-4 | Swindon Town | Avon Combination | - | |
| 12 | 28/8/99 | Cambridge Utd | 1-1 | Notts County | Division 2 | 4329 | |
| 13 | 30/8/99 | Wigan Athletic | 1-1 | Cambridge Utd | Division 2 | 5796 | |
| 14 | 4/9/99 | Cambridge Utd | 1-3 | Stoke City | Division 2 | 4007 | |
| 15 | 7/9/99 | Mildenhall Town | 3-1 | AFC Sudbury | Suffolk Premier Cup | - | Extra time played |
| 16 | 8/9/99 | Cambridge Utd | 2-0 | Wycombe Wanderers | Avon Combination | - | |
| 17 | 11/9/99 | Cambridge Utd | 2-2 | Brentford | Division 2 | 4234 | |
| 18 | 15/9/99 | Cambridge Utd | 2-2 | Barnet | Avon Combination Cup | - | |
| 19 | 18/9/99 | Millwall | 2-1 | Cambridge Utd | Division 2 | 7278 | |
| 20 | 25/9/99 | Cambridge Utd | 2-2 | Gillingham | Division 2 | 4708 | |
| 21 | 29/9/99 | Cambridge Utd | 2-2 | Northampton Town | Avon Combination Cup | - | |
| 22 | 6/10/99 | Cambridge Utd | 2-3 | AFC Bournemouth | Avon Combination | - | |
| 23 | 9/10/99 | Wycombe Wanderers | 1-0 | Cambridge Utd | Division 2 | 5345 | |
| 24 | 16/10/99 | Cambridge Utd | 5-2 | Colchester Utd | Division 2 | 5039 | |
| 25 | 19/10/99 | Cambridge Utd | 0-1 | Burnley | Division 2 | 4434 | |
| 26 | 20/10/99 | Cambridge University | 1-0 | Cambridge Utd | Friendly | - | |
| 27 | 23/10/99 | Gillingham | 2-1 | Cambridge Utd | Division 2 | 6417 | |
| 28 | 30/10/99 | Cambridge Utd | 1-0 | Gateshead | F.A. Cup 1 | 2970 | |
| 29 | 2/11/99 | Cambridge Utd | 1-3 | Scunthorpe Utd | Division 2 | 3285 | |
| 30 | 6/11/99 | Norwich City | 1-0 | Nottingham Forest | Division 1 | 15818 | |
| 31 | 10/11/99 | Cambridge Utd | 2-4 | Peterborough Utd | Avon Combination Cup | - | |
| 32 | 12/11/99 | Cambridge Utd | 3-1 | Luton Town | Divison 2 | 6211 | |
| 33 | 20/11/99 | Cambridge Utd | 1-0 | Bamber Bridge | F.A. Cup 2 | 3303 | |
| 34 | 5/12/99 | Cambridge Utd | 0-2 | AFC Bournemouth | Division 2 | 3579 | |
| 35 | 5/12/99 | Cambridge Utd | 2-0 | Crystal Palace | F.A. Cup 3 | 5631 | |
| 36 | 18/12/99 | Cambridge Utd | 2-3 | Oldham Athletic | Division 2 | 3162 | |
| 37 | 26/12/99 | Oxford Utd | 1-0 | Cambridge Utd | Division 2 | 6772 | |
| 38 | 28/12/99 | Cambridge Utd | 0-0 | Cardiff City | Division 2 | 4250 | |
| 39 | 3/1/00 | Bristol Rovers | 1-0 | Cambridge Utd | Division 2 | 9822 | |
| 40 | 11/1/00 | Cambridge Utd | 1-2 | Barnet | Auto Windscreens Shield 1 | 1556 | Golden goal |
| 41 | 15/1/00 | Reading | 0-0 | Cambridge Utd | Division 2 | 6953 | |
| 42 | 22/1/00 | Cambridge Utd | 2-0 | Chesterfield | Division 2 | 3819 | |
| 43 | 29/1/00 | Cambridge Utd | 1-3 | Bolton Wanderers | F.A. Cup 5 | 7523 | |
| 44 | 5/2/00 | Cambridge Utd | 1-1 | Wigan Athletic | Division 2 | 3755 | |
| 45 | 16/2/00 | Mildenhall Town | 4-0 | Waterbeach | Friendly | - | |
| 46 | 19/2/00 | Cambridge Utd | 0-2 | Blackpool | Division 2 | 4636 | |
| 47 | 26/2/00 | Cambridge Utd | 0-2 | Millwall | Division 2 | 5116 | |
| 48 | 26/2/00 | Brentford | 1-1 | Cambridge Utd | Division 2 | 4987 | |
| 49 | 7/3/00 | Cambridge Utd | 3-0 | Bristol City | Division 2 | 3505 | |
| 50 | 18/3/00 | Cambridge Utd | 3-4 | Wrexham | Division 2 | 4591 | |
| 51 | 21/3/00 | Luton Town | 2-2 | Cambridge Utd | Division 2 | 5379 | |
| 52 | 25/3/00 | Cambridge Utd | 2-0 | Oxford Utd | Division 2 | 5127 | |
| 53 | 1/4/00 | Oldham Athletic | 1-0 | Cambridge Utd | Division 2 | 4988 | |
| 54 | 7/4/00 | Hamburger SV | 1-0 | Hansa Rostock | Bundesliga | 44180 | |
| 55 | 22/4/00 | Colchester Utd | 3-1 | Cambridge Utd | Division 2 | 4902 | |
| 56 | 24/4/00 | Cambridge Utd | 2-0 | Preston | Division 2 | 6068 | |
| 57 | 29/4/00 | Burnley | 2-0 | Cambridge Utd | Division 2 | 15084 | |
| 58 | 6/5/00 | Cambridge Utd | 1-2 | Wycombe Wanderers | Division 2 | 5355 | |