| Liga | Jahr | | Spieltag | Datum | | Heim | Gast | Ergebnis |
| Regionalliga | 1999-2000 | | 2 | 08.08.1999 | | SC Paderborn 07 | LR Ahlen | 0 | 0 |
| Regionalliga | 1999-2000 | | 3 | 11.08.1999 | | SV Eintracht Trier | SC Paderborn 07 | 4 | 1 |
| Regionalliga | 1999-2000 | | 4 | 15.08.1999 | | SC Paderborn 07 | FK Pirmasens | 1 | 1 |
| Regionalliga | 1999-2000 | | 5 | 22.08.1999 | | SC Paderborn 07 | SV 07 Elversberg | 2 | 2 |
| Regionalliga | 1999-2000 | | 6 | 29.08.1999 | | Borussia Dortmund II | SC Paderborn 07 | 3 | 0 |
| Regionalliga | 1999-2000 | | 7 | 05.09.1999 | | SC Paderborn 07 | VfL Bochum II | 1 | 1 |
| Regionalliga | 1999-2000 | | 8 | 12.09.1999 | | Fortuna Düsseldorf | SC Paderborn 07 | 0 | 0 |
| Regionalliga | 1999-2000 | | 9 | 19.09.1999 | | SC Paderborn 07 | KFC Uerdingen 05 | 1 | 0 |
| Regionalliga | 1999-2000 | | 10 | 26.09.1999 | | FSV Salmrohr | SC Paderborn 07 | 1 | 2 |
| Regionalliga | 1999-2000 | | 11 | 03.10.1999 | | SC Paderborn 07 | SC Verl | 0 | 0 |
| Regionalliga | 1999-2000 | | 12 | 10.10.1999 | | SC Preußen Münster | SC Paderborn 07 | 2 | 1 |
| Regionalliga | 1999-2000 | | 13 | 17.10.1999 | | SC Paderborn 07 | TSV Bayer 04 Leverkusen II | 2 | 2 |
| Regionalliga | 1999-2000 | | 14 | 24.10.1999 | | SC 07 Idar-Oberstein | SC Paderborn 07 | 0 | 3 |
| Regionalliga | 1999-2000 | | 15 | 30.10.1999 | | SC Paderborn 07 | Rot-Weiss Essen | 2 | 1 |
| Regionalliga | 1999-2000 | | 16 | 07.11.1999 | | 1. FC Saarbrücken | SC Paderborn 07 | 3 | 0 |
| Regionalliga | 1999-2000 | | 17 | 14.11.1999 | | SC Paderborn 07 | SG Wattenscheid 09 | 1 | 2 |
| Regionalliga | 1999-2000 | | 18 | 28.11.1999 | | Sportfreunde Siegen | SC Paderborn 07 | 1 | 0 |
| Regionalliga | 1999-2000 | | 19 | 05.12.1999 | | SC Paderborn 07 | 1. FC Kaiserslautern II | 0 | 1 |
| Regionalliga | 1999-2000 | | 21 | 18.12.1999 | | LR Ahlen | SC Paderborn 07 | 3 | 1 |
| Regionalliga | 1999-2000 | | 22 | 06.02.2000 | | SC Paderborn 07 | SV Eintracht Trier | 2 | 1 |
| Regionalliga | 1999-2000 | | 23 | 13.02.2000 | | FK Pirmasens | SC Paderborn 07 | 0 | 1 |
| Regionalliga | 1999-2000 | | 24 | 20.02.2000 | | SV 07 Elversberg | SC Paderborn 07 | 2 | 1 |
| Regionalliga | 1999-2000 | | 25 | 26.02.2000 | | SC Paderborn 07 | Borussia Dortmund II | 0 | 2 |
| Regionalliga | 1999-2000 | | 26 | 05.03.2000 | | VfL Bochum II | SC Paderborn 07 | 1 | 4 |
| Regionalliga | 1999-2000 | | 27 | 12.03.2000 | | SC Paderborn 07 | Fortuna Düsseldorf | 0 | 1 |
| Regionalliga | 1999-2000 | | 28 | 19.03.2000 | | KFC Uerdingen 05 | SC Paderborn 07 | 1 | 1 |
| Regionalliga | 1999-2000 | | 29 | 26.03.2000 | | SC Paderborn 07 | FSV Salmrohr | 3 | 0 |
| Regionalliga | 1999-2000 | | 30 | 02.04.2000 | | SC Verl | SC Paderborn 07 | 3 | 1 |
| Regionalliga | 1999-2000 | | 31 | 19.04.2000 | | SC Paderborn 07 | SC Preußen Münster | 3 | 1 |
| Regionalliga | 1999-2000 | | 32 | 15.04.2000 | | TSV Bayer 04 Leverkusen II | SC Paderborn 07 | 0 | 3 |
| Regionalliga | 1999-2000 | | 33 | 24.04.2000 | | SC Paderborn 07 | SC 07 Idar-Oberstein | 2 | 0 |
| Regionalliga | 1999-2000 | | 34 | 30.04.2000 | | Rot-Weiss Essen | SC Paderborn 07 | 2 | 2 |
| Regionalliga | 1999-2000 | | 35 | 07.05.2000 | | SC Paderborn 07 | 1. FC Saarbrücken | 2 | 0 |
| Regionalliga | 1999-2000 | | 36 | 14.05.2000 | | SG Wattenscheid 09 | SC Paderborn 07 | 2 | 0 |
| Regionalliga | 1999-2000 | | 37 | 22.05.2000 | | SC Paderborn 07 | Sportfreunde Siegen | 2 | 1 |
| Regionalliga | 1999-2000 | | 38 | 28.05.2000 | | 1. FC Kaiserslautern II | SC Paderborn 07 | 3 | 2 |
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