| | Liga | Jahr | | Spieltag | Datum | | Heim | Gast | Ergebnis |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 1 | 16.08.1998 | | TuS Einigkeit Hillegossen | VfL Schildesche | 2 | 2 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 2 | 23.08.1998 | | VfL Schildesche | TuS Friedrichsdorf | 2 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 3 | 30.08.1998 | | TSV Amshausen | VfL Schildesche | 2 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 4 | 06.09.1998 | | VfL Schildesche | VfR Wellensiek | 0 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 5 | 13.09.1998 | | SpVg. Heepen | VfL Schildesche | 1 | 6 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 6 | 20.09.1998 | | VfL Schildesche | TSV Oerlinghausen | 1 | 3 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 7 | 27.09.1998 | | TSG Harsewinkel | VfL Schildesche | 0 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 8 | 04.10.1998 | | VfL Schildesche | FC Stukenbrock | 3 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 9 | 11.10.1998 | | 1. FC Isselhorst | VfL Schildesche | 2 | 4 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 10 | 18.10.1998 | | VfL Schildesche | SpVg. Steinhagen | 2 | 3 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 11 | 24.01.1999 | | FC Gütersloh II | VfL Schildesche | 1 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 12 | 08.11.1998 | | VfL Schildesche | VfL Ummeln | 3 | 0 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 13 | 15.11.1998 | | TuS Helpup | VfL Schildesche | 0 | 4 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 14 | 14.04.1999 | | VfL Schildesche | SpVg. Versmold | 4 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 15 | 05.04.1999 | | SC Verl II | VfL Schildesche | 1 | 0 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 16 | 01.04.1999 | | VfL Schildesche | TuS Einigkeit Hillegossen | 1 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 17 | 05.05.1999 | | TuS Friedrichsdorf | VfL Schildesche | 2 | 2 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 18 | 28.02.1999 | | VfL Schildesche | TSV Amshausen | 2 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 19 | 07.03.1999 | | VfR Wellensiek | VfL Schildesche | 1 | 5 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 20 | 14.03.1999 | | VfL Schildesche | SpVg. Heepen | 2 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 21 | 21.03.1999 | | TSV Oerlinghausen | VfL Schildesche | 2 | 4 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 22 | 28.03.1999 | | VfL Schildesche | TSG Harsewinkel | 3 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 23 | 11.04.1999 | | FC Stukenbrock | VfL Schildesche | 1 | 0 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 24 | 18.04.1999 | | VfL Schildesche | 1. FC Isselhorst | 3 | 0 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 25 | 25.04.1999 | | SpVg. Steinhagen | VfL Schildesche | 2 | 2 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 26 | 02.05.1999 | | VfL Schildesche | FC Gütersloh II | 1 | 1 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 27 | 09.05.1999 | | VfL Ummeln | VfL Schildesche | 3 | 2 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 28 | 16.05.1999 | | VfL Schildesche | TuS Helpup | 2 | 2 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 29 | 24.05.1999 | | SpVg. Versmold | VfL Schildesche | 3 | 0 |
| | Bezirksliga Westfalen 2 | 1998-1999 | | 30 | 30.05.1999 | | VfL Schildesche | SC Verl II | 4 | 0 |
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