| Club: | Oldham Athletic |
| Season: | 1999–2000 |
| Manager: | Andy Ritchie |
| Chairman: | David Brierley |
| Stadium: | Boundary Park |
| League: | Second Division |
| League Result: | 14th |
| Cup1: | FA Cup |
| Cup1 Result: | Third round |
| Cup2: | League Cup |
| Cup2 Result: | First round |
| Cup3: | Football League Trophy |
| Cup3 Result: | Second round |
| League Topscorer: | Allott (10) |
| Season Topscorer: | Allott/Whitehall (11) |
| Highest Attendance: | 9,432 vs. Preston North End |
| Lowest Attendance: | 2,750 vs. Stockport County |
| Average Attendance: | 5,391 |
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| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 English football season, Oldham Athletic A.F.C. competed in the Football League Second Division.
In the 1999–2000 season, it began in disastrous fashion with the Latics losing their first five matches and failing to score in the first four. Ritchie's side however recovered well, proving difficult to beat, and losing only four of their nineteen remaining away matches, comfortably finishing in mid-table with 61 points from their 46 league matches.
See main article: 1999–2000 Football League.
Oldham Athletic's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Preston North End | H | 0–1 | 9,432 | ||
| 14 August 1999 | Brentford | A | 0–2 | 5,074 | ||
| 21 August 1999 | Burnley | H | 0–1 | 8,543 | ||
| 28 August 1999 | Oxford United | A | 0–1 | 5,098 | ||
| 4 September 1999 | Gillingham | A | 1–2 | 5,884 | S McNiven | |
| 11 September 1999 | Bury | H | 2–0 | 6,541 | Allott, Duxbury | |
| 18 September 1999 | Bristol Rovers | A | 2–3 | 6,574 | Sheridan, Allott | |
| 25 September 1999 | Reading | A | 1–1 | 7,274 | Allott | |
| 2 October 1999 | Notts County | H | 1–2 | 5,143 | Thom | |
| 9 October 1999 | Luton Town | H | 2–1 | 4,532 | D McNiven, Allott | |
| 16 October 1999 | Cardiff City | A | 1–1 | 5,650 | Graham | |
| 19 October 1999 | Blackpool | A | 2–1 | 3,845 | Duxbury, Allott | |
| 23 October 1999 | Reading | H | 1–2 | 4,963 | Dudley | |
| 2 November 1999 | Wycombe Wanderers | H | 2–2 | 3,807 | Rickers, Whitehall | |
| 6 November 1999 | Chesterfield | A | 1–0 | 2,737 | Adams | |
| 9 November 1999 | Millwall | H | 2–1 | 4,209 | Dudley, Whitehall | |
| 14 November 1999 | Colchester United | H | 1–2 | 5,147 | Dudley | |
| 23 November 1999 | Bristol City | A | 1–1 | 8,214 | Allott | |
| 27 November 1999 | Wrexham | H | 0–0 | 4,963 | ||
| 4 December 1999 | Preston North End | A | 0–2 | 10,970 | ||
| 18 December 1999 | Cambridge United | A | 3–2 | 3,162 | Allott, Adams, Duxbury | |
| 26 December 1999 | Scunthorpe United | H | 1–1 | 5,998 | Whitehall | |
| 28 December 1999 | Stoke City | A | 0–0 | 13,709 | ||
| 3 January 2000 | Bournemouth | H | 1–0 | 5,160 | Allott | |
| 7 January 2000 | Wigan Athletic | A | 1–0 | 6,487 | Duxbury | |
| 15 January 2000 | Brentford | H | 3–0 | 4,967 | Holt, Allott (2, 1 pen) | |
| 22 January 2000 | Burnley | A | 0–3 | 12,391 | ||
| 29 January 2000 | Oxford United | H | 2–0 | 4,780 | Whitehall (2) | |
| 5 February 2000 | Millwall | A | 0–1 | 8,303 | ||
| 12 February 2000 | Gillingham | H | 1–3 | 5,144 | Garnett | |
| 19 February 2000 | Wrexham | A | 3–0 | 3,603 | Graham, Whitehall, Dudley | |
| 26 February 2000 | Bristol Rovers | H | 1–4 | 5,839 | Dudley | |
| 4 March 2000 | Bury | A | 2–2 | 5,306 | Whitehall, Rickers | |
| 11 March 2000 | Wycombe Wanderers | A | 0–0 | 4,471 | ||
| 18 March 2000 | Bristol City | H | 1–1 | 4,808 | Whitehall | |
| 21 March 2000 | Colchester United | A | 1–0 | 3,282 | Holt | |
| 25 March 2000 | Scunthorpe United | A | 2–1 | 3,807 | Garnett, Rickers | |
| 1 April 2000 | Cambridge United | H | 1–0 | 4,988 | Holt | |
| 4 April 2000 | Stoke City | H | 0–1 | 4,474 | ||
| 8 April 2000 | Bournemouth | A | 0–3 | 3,808 | ||
| 11 April 2000 | Wigan Athletic | H | 2–1 | 5,697 | Tipton, Jones | |
| 18 April 2000 | Chesterfield | H | 1–2 | 4,012 | Whitehall | |
| 22 April 2000 | Cardiff City | H | 1–2 | 4,549 | Thom | |
| 24 April 2000 | Notts County | A | 1–0 | 3,728 | Tipton | |
| 29 April 2000 | Blackpool | H | 1–1 | 6,290 | Sugden | |
| 6 May 2000 | Luton Town | A | 1–1 | 5,963 | Tipton (pen) |
See main article: 1999–2000 FA Cup.
| R1 | 30 October 1999 | Chelmsford City | H | 4–0 | 4,392 | Dudley, Sheridan, Duxbury, Whitehall | |
| R2 | 20 November 1999 | Swansea City | H | 1–0 | 4,332 | Whitehall | |
| R3 | 11 December 1999 | Preston North End | A | 1–2 | 9,940 | Adams |
See main article: 1999–2000 Football League Cup.
| R1 1st Leg | 10 August 1999 | Stockport County | A | 0–2 | 3,017 | ||
| R1 2nd Leg | 24 August 1999 | Stockport County | H | 1–1 (lost 1-3 on agg) | 2,750 | Allott |
See main article: 1999–2000 Football League Trophy.
| R2N | 18 January 2000 | Stoke City | H | 0–1 | 4,682 |
Squad at end of season[2]