| 1999-12-28 | ExetervPeterboroLeague Two · England | 2–2 | League Two · England |
| 1999-12-26 | PeterborovRotherhamLeague Two · England | 0–5 | League Two · England |
| 1999-12-04 | HartlepoolvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-11-27 | PeterborovBarnetLeague Two · England | 1–2 | League Two · England |
| 1999-11-20 | PeterborovMacclesfieldLeague Two · England | 2–2 | League Two · England |
| 1999-11-12 | CarlislevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-11-06 | PeterborovShrewsburyLeague Two · England | 4–1 | League Two · England |
| 1999-11-02 | LincolnvPeterboroLeague Two · England | 1–2 | League Two · England |
| 1999-10-23 | PeterborovSouthendLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | TorquayvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-10-16 | HalifaxvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-10-09 | PeterborovChesterLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | PeterborovBrightonLeague Two · England | 0–0 | League Two · England |
| 1999-09-25 | SouthendvPeterboroLeague Two · England | 0–1 | League Two · England |
| 1999-09-18 | PeterborovCheltenhamLeague Two · England | 1–0 | League Two · England |
| 1999-09-11 | YorkvPeterboroLeague Two · England | 0–0 | League Two · England |
| 1999-09-03 | MansfieldvPeterboroLeague Two · England | 3–1 | League Two · England |
| 1999-08-30 | PeterborovDarlingtonLeague Two · England | 4–2 | League Two · England |
| 1999-08-28 | PlymouthvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-08-21 | PeterborovLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1999-08-14 | NorthamptonvPeterboroLeague Two · England | 0–1 | League Two · England |
| 1999-08-07 | PeterborovHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | ScarboroughvPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-05-01 | PeterborovLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 1999-04-24 | CambridgevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-17 | PeterborovTorquayLeague Two · England | 4–0 | League Two · England |
| 1999-04-13 | ScunthorpevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-10 | CarlislevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-05 | PeterborovDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-04-03 | RochdalevPeterboroLeague Two · England | 0–3 | League Two · England |
| 1999-03-28 | PeterborovMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-03-20 | RotherhamvPeterboroLeague Two · England | 2–2 | League Two · England |
| 1999-03-13 | PeterborovSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-03-09 | BrentfordvPeterboroLeague Two · England | 3–0 | League Two · England |
| 1999-03-06 | PeterborovHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1999-02-27 | PlymouthvPeterboroLeague Two · England | 0–2 | League Two · England |
| 1999-02-20 | PeterborovShrewsburyLeague Two · England | 2–2 | League Two · England |
| 1999-02-13 | ChestervPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-02-06 | PeterborovBarnetLeague Two · England | 5–2 | League Two · England |
| 1999-01-30 | BrightonvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-01-26 | PeterborovHullLeague Two · England | 1–1 | League Two · England |
| 1999-01-23 | ExetervPeterboroLeague Two · England | 2–0 | League Two · England |
| 1999-01-16 | PeterborovCardiffLeague Two · England | 2–1 | League Two · England |
| 1999-01-09 | HalifaxvPeterboroLeague Two · England | 2–2 | League Two · England |