| Season | Winners | Result | Runner-up | Venue | Att. | Notes |
| 1876–77 | The Wednesday | 4–3 | Heeley | Bramall Lane | 8,000 | |
| 1877–78 | The Wednesday | 2–0 | Attercliffe | Bramall Lane | 7,000 | |
| 1878–79 | Thursday Wanderers | 3–1 | Heeley | Bramall Lane | 5,000 | |
| 1879–80 | Staveley | 3–1 | Heeley | Sheaf House | | |
| 1880–81 | The Wednesday | 8–1 | Ecclesfield | Bramall Lane | 3,000 | |
| 1881–82 | Heeley | 5–0 | Pyebank | Bramall Lane | 4,000 | |
| 1882–83 | The Wednesday | 2–1 | Lockwood Brothers | Bramall Lane | 4,000 | Replayed final |
| 1883–84 | Lockwood Brothers | - | Middlesbrough | - | | Three semi-finals determined winner and runner-up |
| 1884–85 | Lockwood Brothers | - | Park Grange | - | | Three semi-finals determined winner and runner-up |
| 1885–86 | Mexborough | 2–1 | Heeley | Old Forge Ground | 2,000 | |
| 1886–87 | The Wednesday | 2–1 | Collegiate | Bramall Lane | | |
| 1887–88 | The Wednesday | 3–2 | Ecclesfield | Bramall Lane | 4,000 | |
| 1888–89 | Rotherham Town | 2–1 | Staveley | Bramall Lane | | |
| 1889–90 | Rotherham Town | 1–0 | Sheffield United | Rotherham | | |
| 1890–91 | Doncaster Rovers | 2–1 | Sheffield United | Bramall Lane | | |
| 1891–92 | Sheffield United | 2–1 | The Wednesday reserves | Bramall Lane | 5,000 | |
| 1892–93 | Sheffield United reserves | 3–1 | The Wednesday reserves | Bramall Lane | 4,500 | |
| 1893–94 | Mexborough | - | Sheffield United reserves | - | | League format |
| 1894–95 | The Wednesday reserves | - | Sheffield United reserves | - | | League format |
| 1895–96 | Mexborough | - | Sheffield United reserves | - | | League format |
| 1896–97 | Sheffield United reserves | 3–0 | Wath | Olive Grove | | |
| 1897–98 | Sheffield United reserves | 3–1 | The Wednesday reserves | Bramall Lane | 2,000 | |
| 1898–99 | Sheffield United reserves | 5–2 | Attercliffe | Bramall Lane | | Replayed final |
| 1899–1900 | The Wednesday reserves | 2–0 | Worksop Town | Carbrook | | |
| 1900–01 | Sheffield United reserves | 6–1 | Channing Rovers | Bramall Lane | | |
| 1901–02 | The Wednesday reserves | 1–0 | Royston United | Millmoor | 3,000 | |
| 1902–03 | The Wednesday reserves | 5–0 | Roundel | Bramall Lane | 10,000 | Replayed final |
| 1903–04 | Barnsley reserves | 6–1 | Hallam | Bramall Lane | | |
| 1904–05 | Sheffield United reserves | 3–1 | The Wednesday reserves | Hillsborough | 6,000 | |
| 1905–06 | Denaby United | 4–2 | The Wednesday reserves | Clifton Lane | 7,000 | |
| 1906–07 | The Wednesday reserves | 2–0 | Sheffield United reserves | Bramall Lane | 4,000 | Replayed final |
| 1907–08 | Sheffield United reserves | 1–0 | South Kirkby Colliery | Hillsborough | | |
| 1908–09 | Sheffield United reserves | 5–1 | Rotherham County | Bramall Lane | 3,384 | Replayed final |
| 1909–10 | Denaby United | - | Barnsley reserves | - | | Awarded to Denaby United |
| 1910–11 | Sheffield United reserves | 4–1 | Mexborough Town | Clifton Lane | | |
| 1911–12 | Doncaster Rovers | 3–0 | Sheffield United reserves | Wath | | |
| 1912–13 | Rotherham County | 3–0 | Worksop Town | Bramall Lane | | |
| 1913–14 | Rotherham County | 1–0 | The Wednesday reserves | Bramall Lane | 8,000 | |
| 1914–15 | Barnsley reserves | 3–0 | Worksop Town | Bramall Lane | | |
| 1919–20 | Rotherham Town | 1–0 | Sheffield United reserves | Clifton Lane | | |
| 1920–21 | The Wednesday reserves | 2–0 | Barnsley reserves | Bramall Lane | 8,000 | |
| 1921–22 | The Wednesday reserves | 2–0 | Barnsley reserves | Bramall Lane | | |
| 1922–23 | Wombwell | 2–0 | Mexborough Town | Wath | | Replayed final |
| 1923–24 | Worksop Town | 3–0 | Barnsley reserves | Bramall Lane | | |
| 1924–25 | Rotherham Town | 5–1 | Worksop Town | Bramall Lane | | |
| 1925–26 | Wath Athletic | 4–0 | Hemsworth West End | Tickhill Square | | |
| 1926–27 | Darfield | 5–2 | Ecclesfield United | Birdwell | | |
| 1927–28 | Frickley Colliery | 3–1 | Ardsley Athletic | Hampden Road | | |
| 1928–29 | Ardsley Athletic | 6–2 | Ecclesfield United | Birdwell | | |
| 1929–30 | South Kirkby Colliery | 2–0 | Cudworth Village | Cemetery Road | | Replayed final |
| 1930–31 | Mexborough Athletic | 2–0 | Frickley Colliery | Hampden Road | | |
| 1931–32 | Dinnington Athletic | 3–0 | South Kirkby Colliery | Hampden Road | | |
| 1932–33 | Denaby United | 1–0 | Rawmarsh Welfare | Hampden Road | | Replayed final |
| 1933–34 | Mexborough Athletic | 8–1 | Woodhouse Alliance | Tickhill Square | | |
| 1934–35 | Firbeck Main Colliery | 3–0 | Denaby United | Dinnington | | |
| 1935–36 | Denaby United | 4–2 | Worksop Town | Central Avenue | | |
| 1936–37 | Upton Colliery | 4–3 | Thurnscoe Victoria | Hampden Road | | |
| 1937–38 | Norton Woodseats | 2–1 | Lopham Street UM | Hillsborough | | |
| 1938–39 | Rawmarsh Welfare | 3–2 | Worksop Town | Beighton | | |
| 1939–40 | Beighton Miners Welfare | 2–1 | Frickley Colliery Athletic | Belle Vue | | Replayed final |
| 1940–41 | South Kirkby Colliery | 2–1 | Beighton Miners Welfare | Millmoor | | Replayed final |
| 1941–42 | Manvers Main | 1–0 | Sheffield United reserves | Bramall Lane | | |
| 1942–43 | Royal Army Service Corps | 1–0 | Sheffield Wednesday reserves | Bramall Lane | | Replayed final |
| 1943–44 | Royal Army Service Corps | 5–3 | Norton Woodseats | Millmoor | | |
| 1944–45 | Barnsley reserves | 3–1 | Brodsworth Welfare | Oakwell | | |
| 1945–46 | Wombwell Athletic | 2–0 | Harworth Colliery | Wath | | |
| 1946–47 | Thurcroft Main | W – L | Dinnington Athletic | | | |
| 1947–48 | Harworth Colliery | 1–0 | Beighton Miners Welfare | Central Avenue | | |
| 1948–49 | Royston Social | 3–2 | Harworth Colliery | Central Avenue | | |
| 1949–50 | Upton Colliery | 5–3 | Beighton Miners Welfare | Tickhill Square | | |
| 1950–51 | Hallam | 3–0 | Stocksbridge Works | Hillsborough | 7,240 | |
| 1951–52 | Stocksbridge Works | 4–1 | Denaby United | Hillsborough | | |
| 1952–53 | Worksop Town | 3–1 | Beighton Miners Welfare | Hillsborough | | |
| 1953–54 | Sheffield Wednesday 'A' | 2–1 | Worksop Town | Central Avenue | | |
| 1954–55 | Worksop Town | 2–1 | Stocksbridge Works | Central Avenue | | |
| 1955–56 | Beighton Miners Welfare | 4–2 | Stocksbridge Works | Thorncliffe | | |
| 1956–57 | Frickley Colliery | 3–2 | Worksop Town | Westfield Lane | | |
| 1957–58 | Bentley Colliery | 3–1 | Stocksbridge Works | Oakwell | | |
| 1958–59 | Bentley Colliery | 1–0 | Yotar Sports | Tickhill Square | | |
| 1959–60 | Grimethorpe Miners Welfare | 3–2 | Denaby United | Grimethorpe | | |
| 1960–61 | Frickley Colliery | 2–0 | Worksop Town | Westfield Lane | | Replayed final |
| 1961–62 | Hallam | 1–0 | Sheffield | High Green | | Replayed final |
| 1962–63 | Frickley Colliery | 2–1 | Sheffield United 'A' | Hampden Road | | |
| 1963–64 | Mexborough Town | - | Stocksbridge Works | - | | Awarded to Mexborough Town |
| 1964–65 | Hallam | 3–2 | Thurcroft Welfare | Millmoor | | |
| 1965–66 | Worksop Town | 3–2 | Frickley Colliery | Westfield Lane | | |
| 1966–67 | Frickley Colliery | 4–1 | Norton Woodseats | Coach & Horses Ground | | |
| 1967–68 | Hallam | 1–0 | Norton Woodseats | Hillsborough | | |
| 1968–69 | Redfearn Sports | 1–0 | Frickley Colliery | Tickhill Square | | |
| 1969–70 | Worksop Town | 2–1 | Dinnington Athletic | Hard Lane | | |
| 1970–71 | Rawmarsh Welfare | 3–1 | Frickley Colliery | Dale Road | | |
| 1971–72 | Kiveton Park | 3–0 | | Swallownest | | |
| 1972–73 | Worksop Town | 4–1 | Worsborough Bridge Miners Welfare | Millmoor | | |
| 1973–74 | Frecheville Community Association | 2–1 | Worksop Town | Hard Lane | | Replayed final |
| 1974–75 | Mexborough Town Athletic | 1–0 | Denaby United | Tickhill Square | | |
| 1975–76 | Emley | 2–0 | Worksop Town | Hillsborough | | |
| 1976–77 | Mexborough Town Athletic | 2–1 | Worksop Town | Bramall Lane | | |
| 1977–78 | Maltby Miners Welfare | 2–1 | Mexborough Town Athletic | Belle Vue | | |
| 1978–79 | Frickley Athletic | 3–2 | Mexborough Town Athletic | Hampden Road | | |
| 1979–80 | Emley | 2–0 | Worksop Town | Oakwell | | |
| 1980–81 | Emley | 2–1 | Frickley Athletic | Woolley Colliery Road | | |
| 1981–82 | Worksop Town | - | Frickley Athletic | - | | Awarded to Worksop Town |
| 1982–83 | Mexborough Town Athletic | 3–1 | Denaby United | Millmoor | | |
| 1983–84 | Emley | 2–0 | | Oakwell | | |
| 1984–85 | Worksop Town | 2–1 | Frickley Athletic | Millmoor | | |
| 1985–86 | Frickley Athletic | 2–0 | Crookes | Central Avenue | | |
| 1986–87 | Denaby United | 3–2 | Emley | Oakwell | | |
| 1987–88 | Frickley Athletic | 2–1 | Worksop Town | | | Played over two legs |
| 1988–89 | Emley | 2–0 | Woolley Miners Welfare | Oakwell | | |
| 1989–90 | Frickley Athletic | 2–1 | Denaby United | | | Played over two legs |
| 1990–91 | Emley | 1–1 | Worksop Town | Hillsborough | | Emley won on penalties |
| 1991–92 | Emley | 1–0 | Frickley Athletic | Bracken Moor | 1,300 | |
| 1992–93 | Stocksbridge Park Steels | 5–3 | Worksop Town | | | Played over two legs |
| 1993–94 | Sheffield | 1–1 | Worksop Town | Hillsborough | 698 | Sheffield won on penalties |
| 1994–95 | Worksop Town | 1–0 | Emley | Hillsborough | 750 | |
| 1995–96 | Stocksbridge Park Steels | 1–0 | Grimethorpe Miners Welfare | Welfare Ground | | |
| 1996–97 | Worksop Town | 7–0 | Harworth Colliery Institute | Hillsborough | 700 | |
| 1997–98 | Emley | 3–0 | Parkgate | Hillsborough | 1,200 | |
| 1998–99 | Stocksbridge Park Steels | 1–0 | Emley | Hillsborough | 2,000 | |
| 1999–2000 | Frickley Athletic | 3–0 | Emley | Hillsborough | | |
| 2000–01 | Doncaster Rovers | 2–1 | Emley | Hillsborough | 1,486 | |
| 2001–02 | Doncaster Rovers | 3–0 | Emley | Hillsborough | 973 | |
| 2002–03 | Worksop Town | 2–1 | Doncaster Rovers | Hillsborough | 813 | |
| 2003–04 | Frickley Athletic | 3–2 | Worksop Town | Hillsborough | 882 | |
| 2004–05 | Sheffield | 1–0 | Worksop Town | Hillsborough | 821 | |
| 2005–06 | Sheffield | 2–1 | Parkgate | Hillsborough | 666 | |
| 2006–07 | Stocksbridge Park Steels | 2–1 | Worksop Town | Hillsborough | 446 | |
| 2007–08 | Sheffield | 2–0 | Worksop Town | Hillsborough | 583 | |
| 2008–09 | Stocksbridge Park Steels | 3–0 | Brodsworth Welfare | Hillsborough | 338 | |
| 2009–10 | Sheffield | 4–2 | Hallam | Hillsborough | 546 | |
| 2010–11 | Stocksbridge Park Steels | 3–0 | Parkgate | Hillsborough | 440 | |
| 2011–12 | Worksop Town | 3–2 | Frickley Athletic | Hillsborough | 850 | |
| 2012–13 | Frickley Athletic | 4–3 | Sheffield | Hillsborough | 487 | |
| 2013–14 | Athersley Recreation | 1–0 | Frickley Athletic | Hillsborough | 607 | |
| 2014–15 | Frickley Athletic | 4–1 | Nostell Miners Welfare | New York Stadium | 465 | |
| 2015–16 | Frickley Athletic | | Shaw Lane Aquaforce | | – | Awarded to Frickley Athletic |
| 2016–17 | Shaw Lane | 1–0 | Frickley Athletic | Bramall Lane | 451 | |
| 2017–18 | Shaw Lane | 4–3 | Penistone Church | Bramall Lane | 671 | |
| 2018–19 | North Gawber Colliery | | Frickley Athletic | | – | Awarded to North Gawber Colliery |
| 2021–22 | Worksop Town | 3–0 | Maltby Main | Eco-Power Stadium | 1,044 | |
| 2022–23 | Emley | 2–0 | Maltby Main | Eco-Power Stadium | 640 | |
| 2023–24 | Worksop Town | 5–0 | Penistone Church | Hillsborough | 1,500 | |
| 2024–25 | Worksop Town | 2–1 | Hallam | Hillsborough | 2,614 | |