The 1938–39 season was the 41st in the history of the Southern League. Colchester United won the title.[1] Three clubs applied to join the Football League, although none were successful. The following season saw the league split into Eastern and Western sections as part an emergency war-time competition, after which the league was discontinued until the end of World War II.
| Competition: | Southern Football League |
| Season: | 1938–39 |
| Winners: | Colchester United (1st title) |
| Promoted: | none |
| Matches: | 506 |
| Total Goals: | 1855 |
| Prevseason: | 1937–38 |
| Nextseason: | 1939–40 |
A total of 23 teams contest the division, including 17 sides from previous season, one team relegated from The Football League and five new teams.
Team relegated from 1937–38 Football League:
Newly elected teams:
Three Southern League clubs, Chelmsford City, Colchester United and Gillingham, applied to join the Football League. However, both League clubs were re-elected.[2]
| Club | League | Votes | |
|---|---|---|---|
| Bristol Rovers | Football League Third Division South | 45 | |
| Walsall | Football League Third Division South | 36 | |
| Gillingham | Southern League | 15 | |
| Chelmsford City | Southern League | 1 | |
| Colchester United | Southern League | 1 |