The 2008–09 season was the 106th in the history of the Southern League, which is an English football competition featuring semi-professional and amateur clubs from the South West, South Central and Midlands of England and South Wales. At the end of the season Division One Midlands was renamed Division One Central.

Premier Division

The Premier Division consisted of 22 clubs, including 17 clubs from the previous season and five new clubs: Corby Town won the Premier Division and along with play-off winners Gloucester City got a place in the Conference North next year. Mangotsfield United, Yate Town and Hitchin Town relegated to the divisions One, while Banbury United were reprieved from relegation after two Conference South clubs folded.

League table

Play-offs

Results

Stadia and locations

Division One Midlands

Division One Midlands consisted of 22 clubs, including 14 clubs from previous season and eight new clubs: Nuneaton Borough, finished 7th in the Conference North went into liquidation due to financial difficulties, were immediately reformed under the name Nuneaton Town and placed two divisions below in Midlands division. Leamington won the division in the second attempt and got a place in Premier Division along with play-off winners Nuneaton Town. Dunstable and Malvern finished bottom of the table and were relegated to the lower leagues. At the end of the season Division One Midlands was renamed Division One Central.

League table

Play-offs

Results

Stadia and locations

Division One South & West

Division One South & West consisted of 22 clubs, including 15 clubs from previous season and seven new clubs: Truro City won the division in an inaugural season and got a place in Premier Division along with play-off winners Didcot Town. Bracknell Town finished second bottom but were reprieved from relegation due to higher league clubs' problems. Winchester City finished bottom of the table and were relegated to the lower league.

League table

Play-offs

Results

Stadia and locations

League Cup

Preliminary round

First round

Second round

Third round

Quarterfinals

Semifinals

Final