The 1995–96 South Midlands League season was 67th in the history of South Midlands League.[1]
| Competition: | South Midlands League Premier Division |
| Season: | 1995–96 |
| Winners: | Arlesey Town |
| Promoted: | None |
| Relegated: | None |
| Prevseason: | 1994–95 |
| Nextseason: | 1996–97 |
The Premier Division featured 15 clubs which competed in the division last season, along with 2 new clubs, promoted from last season's Senior Division:
| Competition: | South Midlands League Senior Division |
| Season: | 1995–96 |
| Winners: | Holmer Green |
| Promoted: | Bedford United |
| Relegated: | None |
| Prevseason: | 1994–95 |
| Nextseason: | 1996–97 |
The Senior Division featured 11 clubs which competed in the division last season, along with 3 new clubs:
| Competition: | South Midlands League Division One |
| Season: | 1995–96 |
| Winners: | Mercedes Benz |
| Promoted: | Mercedes Benz |
| Relegated: | None |
| Prevseason: | 1994–95 |
| Nextseason: | 1996–97 |
The Division One featured 10 clubs which competed in the division last season, along with 7 new clubs: