| Founded | 1932 |
|---|---|
| Region |  England |
| Website | Southern League Website |
 2023–24 | |
The Southern League Cup is a knock-out cup competition organised by the Southern Football League. For the 2017–18 season, the competition was known as the BigFreeBet.com Challenge Cup for sponsorship reasons. It is understood that the majority of funds from the sponsorship deal are being put into developing English grassroots football.[1]
| Season | Champions | Result | Runners-up | Ref. |
|---|---|---|---|---|
| 1932–33 | Plymouth Argyle Reserves (WD) | [2] | ||
| 1933–34 | Plymouth Argyle Reserves (WD) | |||
| 1934–35 | Folkestone (ED) | |||
| 1935–36 | Plymouth Argyle Reserves (WD) | |||
| 1936–37 | Newport County Reserves (SL) | |||
| 1937–38 | Colchester United (SL) | |||
| 1938–39 | Not completed[2] | |||
| 1939–40 | Worcester City (WS) | |||
| 1945–46 | Chelmsford City (SL) | |||
| 1946–47 | Gillingham (SL) | |||
| 1947–48 | Merthyr Tydfil (SL) | |||
| 1948–49 | Yeovil Town SL) | |||
| 1949–50 | Colchester United (SL) | |||
| 1950–51 | Merthyr Tydfil (SL) | |||
| 1951–52 | Hereford United (SL) | |||
| 1952–53 | Headington United (SL) | |||
| 1953–54 | Headington United (SL) | |||
| 1954–55 | Yeovil Town (SL) | |||
| 1955–56 | Gloucester City (SL) | |||
| 1956–57 | Hereford United (SL) | |||
| 1957–58 | Cheltenham Town (SL) | |||
| 1958–59 | Hereford United (NW-D) | |||
| 1959–60 | Chelmsford City (PD) | |||
| 1960–61 | Yeovil Town (PD) | |||
| 1961–62 | Cambridge United (PD) | |||
| 1962–63 | Guildford City (PD) | |||
| 1963–64 | Burton Albion (D1) | |||
| 1964–65 | Cambridge United (PD) | |||
| 1965–66 | Yeovil Town (PD) | |||
| 1966–67 | Guildford City (PD) | |||
| 1967–68 | Margate (PD) | |||
| 1968–69 | Cambridge United (PD) | |||
| 1969–70 | Wimbledon (PD) | |||
| 1970–71 | Telford United (PD) | |||
| 1971–72 | Barnet (PD) | |||
| 1972–73 | Weymouth (PD) | |||
| 1973–74 | AP Leamington (D1N) | |||
| 1974–75 | Kettering Town (PD) | |||
| 1975–76 | Wimbledon (PD) | |||
| 1976–77 | Dartford (PD) | |||
| 1977–78 | Gravesend & Northfleet (PD) | |||
| 1978–79 | Bath City (PD) | |||
| 1979–80 | Kidderminster Harriers (MD) | |||
| 1980–81 | Bedford Town (MD) | |||
| 1981–82 | Wealdstone (MD) | |||
| 1982–83 | Alvechurch (PD) | |||
| 1983–84 | AP Leamington (PD) | |||
| 1984–85 | Fisher Athletic (PD) | |||
| 1985–86 | Bromsgrove Rovers (MD) | |||
| 1986–87 | Waterlooville (SD) | |||
| 1987–88 | Dartford (PD) | |||
| 1988–89 | Dartford (PD) | |||
| 1989–90 | VS Rugby (PD) | |||
| 1990–91 | Chelmsford City (PD) | |||
| 1992–93 | Stourbridge (MD) | |||
| 1993–94 | Sudbury Town (SD) | |||
| 1994–95 | Hastings Town (PD) | |||
| 1995–96 | Nuneaton Borough (MD) | |||
| 1996–97 | Burton Albion (PD) | |||
| 1997–98 | Margate (SD) | |||
| 1998–99 | Sutton Coldfield Town (PD) | 2-1 aggregate | Cambridge City (PD) | |
| 1999–00 | Burton Albion (PD) | |||
| 2000–01 | Worcester City (PD) | |||
| 2001–02 | Dorchester Town (ED) | |||
| 2002–03 | Crawley Town (PD) | |||
| 2003–04 | Crawley Town (PD) | |||
| 2004–05 | King's Lynn (PD) | |||
| 2005–06 | Hitchin Town (PD) | |||
| 2006–07 | Tiverton Town (PD) | 1-0, 2-2 | Hemel Hempstead Town (PD) | |
| 2007–08 | Hillingdon Borough (PD) | 1-1, 3-0 | Clevedon Town (SW) | |
| 2008–09 | Atherstone Town (MD) | 2-1, 3-1 | Bridgwater Town (SW) | |
| 2009–10 | Cambridge City (PD) | 1-0, 0-1 (4-2)p | VT (SW) | |
| 2010–11 | Hednesford Town (PD) | 2-1, 3-0 | Hemel Hempstead Town (PD) | |
| 2011–12 | Clevedon Town (SW) | 0-0, 2-1 | Banbury United (PD) | |
| 2012–13 | Arlesey Town (PD) | 1-0, 1-1 | Frome Town (PD) | |
| 2013–14 | St Neots Town (PD) | 0-0, 1-0 | Tiverton Town (SW) | |
| 2014–15 | Poole Town (PD) | 1-1, 0-0 | Corby Town (PD) | |
| 2015–16 | Merthyr Town (PD) | 5-1, 2-0 | Cambridge City (PD) | |
| 2016–17 | Hayes & Yeading United (PD) | 1-1 (4-2)p | St Ives Town (PD) | |
| 2017–18 | Hitchin Town (PD) | 1-0 | Didcot Town (DOW) | |
| 2018–19 | Stratford Town (PDC) | 1-0 | Cinderford Town (DOS) | [3] |
| 2019–20 | No winner | |||
| 2020–21 | No winner | |||
| 2021–22 | Royston Town (PDC) | 2-0, 5-0 | Taunton Town (PDS) | [4] |
| 2022–23 | No winner | |||