The 1999–2000 West Midlands (Regional) League season was the 100th in the history of the West Midlands (Regional) League, an English association football competition for semi-professional and amateur teams based in the West Midlands county, Shropshire, Herefordshire, Worcestershire and southern Staffordshire.
| Competition: | West Midlands League Premier Division |
| Season: | 1999–2000 |
| Winners: | Stafford Town |
| Promoted: | Stafford Town |
| Matches: | 462 |
| Total Goals: | 1528 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The Premier Division featured 19 clubs which competed in the division last season, along with three new clubs: