1999–2000 Stockport County F.C. season
During the 1999–2000 English football season, Stockport County F.C. competed in the Football League First Division.
Season summary
In the 1999–2000 season, Andy Kilner replaced Gary Megson as Stockport's manager in the summer. Stockport had a brilliant first half of the campaign and on Boxing Day, they sat in the play-off places but afterwards came a dramatic slide in form with just 2 wins from the next 22 league games and Stockport finished the season in a disappointing 17th place.Final league table
Results
Stockport County's score comes firstLegend
Football League First Division
FA Cup
| Round | Date | Opponent | Venue | Result | Attendance | Goalscorers |
| R3 | 11 December 1999 | Grimsby Town | A | 2–3 | 3,400 | Bailey, Thomas-Moore |
League Cup
| Round | Date | Opponent | Venue | Result | Attendance | Goalscorers |
| R1 1st Leg | 10 August 1999 | Oldham Athletic | H | 2–0 | 3,017 | Cooper, Angell |
| R1 2nd Leg | 24 August 1999 | Oldham Athletic | A | 1–1 | 2,750 | Woodthorpe |
| R2 1st Leg | 14 September 1999 | Barnsley | A | 1–1 | 6,966 | Briggs |
| R2 2nd Leg | 21 September 1999 | Barnsley | H | 3–3 | 3,332 | Wilbraham, D'Jaffo, Dinning |