The 2005–06 West Midlands (Regional) League season was the 106th 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. It has three divisions, the highest of which is the Premier Division, which sits at step 6 of the National League System, or the tenth level of the overall English football league system.
| Competition: | West Midlands League Premier Division |
| Season: | 2005–06 |
| Winners: | Market Drayton Town |
| Promoted: | Market Drayton Town |
| Matches: | 462 |
| Total Goals: | 1498 |
| Prevseason: | 2004–05 |
| Nextseason: | 2006–07 |
The Premier Division featured 18 clubs which competed in the division last season, along with four new clubs:
Also, Smethwick Sikh Temple changed name to Smethwick Rangers.