| | | Winners | | Runners Up |
| 1927/28 | | Blackheath Town | | Kidderminster Harriers Res |
| 1928/29 | | Blackheath Town | | Halesowen Labour |
| 1929/30 | | Halesowen Labour | | Netherton Liberals |
| 1929/30 | | Dudley Town | | Bewdley |
| 1930/31 | | Halesowen Labour | | Dudley Town |
| 1931/32 | | Dudley Town | | Brierley Hill Alliance Res |
| 1932/33 | | Tarmac | | Lye Town |
| 1933/34 | | Woodside Wdrs | | Tarmac |
| 1934/35 | | Catshill Village | | Lye Town |
| 1935/36 | | Lye Town | | Catshill Village |
| 1936/37 | | Catshill Village | | Goodyears |
| 1937/38 | | Catshill Village | | Lye Town |
| 1938/39 | | Catshill Village | | Wrockwardine Wood |
| 1948/49 | | Jack Mould's Ath | | Smethwick Highfield |
| 1949/50 | | Bournville Ath | | Jack Mould's Ath |
| 1950/51 | | Jack Mould's Ath | | Smethwick Highfield |
| 1951/52 | | Walsall Wood | | Smethwick Highfield |
| 1952/53 | | Evesham Utd | | Smethwick Highfield |
| 1953/54 | | Brierley Hill Alliance Res | | Walsall Wood |
| 1954/55 | | Evesham Utd | | Walsall Wood |
| 1955/56 | | Malvern Town | | Stratford Town |
| 1956/57 | | Stratford Town | | Wolves 'B' |
| 1957/58 | | Wolves 'B' | | Walsall Wood |
| 1958/59 | | Shelfield Ath | | Walsall Wood |
| 1959/60 | | Paget Rgrs | | Shelfield Ath |
| 1960/61 | | Paget Rgrs | | Walsall Wood |
| 1961/62 | | Allens Cross | | Jack Mould's Ath |
| 1962/63 | | Alvechurch | | Wolves 'B' |
| 1963/64 | | Hall Green Ams | | Alvechurch |
| 1964/65 | | Alvechurch | | Hall Green Ams |
| 1965/66 | | Evesham Utd | | Alvechurch |
| 1966/67 | | Alvechurch | | Evesham Utd |
| 1967/68 | | Evesham Utd | | Alvechurch |
| 1968/69 | | Evesham Utd | | Alvechurch |
| 1969/70 | | Paget Rgrs | | Sutton Coldfield Town |
| 1970/71 | | Paget Rgrs | | Sutton Coldfield Town |
| 1971/72 | | Alvechurch | | Oldbury Utd |
| 1972/73 | | Highgate Utd | | Alvechurch |
| 1973/74 | | Highgate Utd | | Malvern Town |
| 1974/75 | | Highgate Utd | | Moor Green |
| 1975/76 | | Northfield Town | | Moor Green |
| 1976/77 | | Blakenall | | Bridgnorth Town |
| 1977/78 | | Sutton Coldfield Town | | Paget Rgrs |
| 1978/79 | | Sutton Coldfield Town | | Oldbury Utd |
| 1979/80 | | Bridgnorth Town | | Moor Green |
| 1980/81 | | Moor Green | | Bridgnorth Town |
| 1981/82 | | Chipping Norton Town | | Highgate Utd |
| 1982/83 | | Bridgnorth Town | | Moor Green |
| 1983/84 | | Studley Sporting | | Coleshill Town |
| 1984/85 | | Mile Oak Rvrs | | Solihull Borough |
| 1985/86 | | Boldmere St. Michaels | | Paget Rgrs |
| 1986/87 | | Stratford Town | | Paget Rgrs |
| 1987/88 | | Racing Club Warwick | | Boldmere St. Michaels |
| 1988/89 | | Boldmere St. Michaels | | Racing Club Warwick |
| 1989/90 | | Boldmere St. Michaels | | Northfield Town |
| 1990/91 | | West Midlands Police | | Solihull Borough |
| 1991/92 | | Evesham Utd | | Armitage '90 |
| 1992/93 | | Armitage '90 | | Stapenhill |
| 1993/94 | | Pershore Town | | West Midlands Police |
| 1994/95 | | Northfield Town | | Bloxwich Town |
| 1995/96 | | Bloxwich Town | | Coventry Sphinx |
| 1996/97 | | Richmond Swifts | | Meir KA |
| 1997/98 | | Worcester Athletico | | Southam Utd |
| 1998/99 | | Alveston | | Cheslyn Hay |
| 1999/00 | | Nuneaton Griff | | Kings Heath |
| 2000/01 | | Nuneaton Griff | | Studley BKL |
| 2001/02 | | Grosvenor Park | | Coventry Sphinx |
| 2002/03 | | Alvechurch | | Coventry Marconi |
| 2003/04 | | Romulus | | Leamington |
| 2004/05 | | Leamington | | Coventry Sphinx |
| 2005/06 | | Atherstone Town | | Coventry Sphinx |
| 2006/07 | | | | |