- 1891–92 – Middlesbrough Swifts
- 1892–93 – South Bank
- 1893–94 – Darlington St. Hilda's
- 1894–95 – Middlesbrough Dự bị
- 1895–96 – Darlington Dự bị
- 1896–97 – Thornaby
- 1897–98 – Thornaby
- 1898–99 – Haverton Hill
- 1899–1900 – Haverton Hill
- 1900–01 – Haverton Hill
- 1901–02 – Darlington St. Hilda's
- 1902–03 – Thornaby St. Patrick's
- 1903–04 – Thornaby St. Patrick's
- 1904–05 – South Bank St. Peter's
- 1905–06 – Riley Bros (Stockton)
- 1906–07 – Thornaby St. Patrick's
- 1907–08 – West Hartlepool Expansion
- 1908–09 – Skinningrove United
- 1909–10 – Eston United
- 1910–11 – Thornaby St. Patrick's
- 1911–12 – Ashmore, Benson & Pease
- 1912–13 – Cleveland Chemical Works
- 1914–18 – Not competed for due to World War I
- 1919–20 – Haverton Hill
- 1920–21 – Blair & Co.
- 1921–22 – Stillington St. John's
- 1922–23 – West Hartlepool Temp
- 1923–24 – Stockton Malleable Institute
- 1924–25 – Normanby Magnesite
- 1925–26 – Stockton Malleable Institute
- 1926–27 – West Hartlepool Peser
- 1927–28 – Normanby Magnesite
- 1928–29 – West Hartlepool Peser
- 1929–30 – West Hartlepool Peser
- 1930–31 – South Bank East End
- 1931–32 – Normanby Magnesite
- 1932–33 – South Bank St. Peter's
- 1933–34 – Grangetown St. Mary's
- 1934–35 – Lingdale
- 1935–36 – Carlin How
- 1936–37 – South Bank East End
- 1937–38 – South Bank East End
- 1938–39 – Cargo Fleet Athletic
- 1939–40 – South Bank Athletic
- 1941–46 – Not competed for due to World War II
- 1946–47 – Port Clarence Sports & Social Club
- 1947–48 – Port Clarence Sports & Social Club
- 1948–49 – Head Wrightson
- 1949–50 – Portrack Shamrocks
- 1950–51 – Ashmore Recreation
- 1951–52 – Billingham Synthonia Dự bị
- 1952–53 – Head Wrightson
- 1953–54 – Stockton Amateurs
- 1954–55 – ICI Wilton
- 1955–56 – Portrack Shamrocks
- 1956–57 – Redcar Albion
| - 1957–58 – Redcar Albion
- 1958–59 – Redcar Albion
- 1959–60 – Cleveland Mines
- 1960–61 – Cleveland Mines
- 1961–62 – Billingham Synthonia Dự bị
- 1962–63 – Billingham Synthonia Dự bị
- 1963–64 – Billingham Synthonia Dự bị
- 1964–65 – Acklam Steelworks
- 1965–66 – Acklam Steelworks
- 1966–67 – Head Wrightson
- 1967–68 – Head Wrightson
- 1968–69 – Head Wrightson
- 1969–70 – Whinney Banks
- 1970–71 – Winterton Hospital
- 1971–72 – Whinney Banks
- 1972–73 – Teesside Polytechic
- 1973–74 – Cassel Works
- 1974–75 – Hartlepool Boys Welfare Old Boys
- 1975–76 – Acklam Steelworks
- 1976–77 – Billingham Social Club
- 1977–78 – Smith's Dock
- 1978–79 – Billingham Social Club
- 1979–80 – Smith's Dock
- 1980–81 – Marske United
- 1981–82 – Hartlepool Athletic
- 1982–83 – Hartlepool Athletic
- 1983–84 – Marske United
- 1984–85 – Hartlepool Boys Welfare Old Boys
- 1985–86 – Stockton Town
- 1986–87 – New Marske Sports Club
- 1988–89 – Hemlngton Sports Club
- 1989–90 – Nunthorpe Athletic
- 1990–91 – ICI Wilton
- 1991–92 – Billingham Cassel Mall
- 1992–93 – Rowntrees
- 1993–94 – Rowntrees
- 1994–95 – Tees Components
- 1995–96 – Acklam Steelworks
- 1996–97 – Acklam Steelworks
- 1997–98 – Acklam Steelworks
- 1998–99 – Grangetown Boys Club
- 1999–2000 – Grangetown Boys Club
- 2000–01 – Acklam Steelworks
- 2001–02 – Grangetown Boys Club
- 2002–03 – Grangetown Boys Club
- 2003–04 – Hartlepool
- 2004–05 – Carlin How Working Mens Club
- 2005–06 – Carlin How Working Mens Club
- 2006–07 – Carlin How Working Mens Club
- 2007–08 – Beechwood, Easterside & District Social
- 2008–09 – Beechwood, Easterside & District Social
- 2009–10 – Beechwood, Easterside & District Social
- 2010–11 – Grangetown Boys Club
- 2011–12 – Richmond Town
- 2012–13 – Endeavour
- 2013–14 – Whinney Banks Youth & Community Centre
- 2014–15 – Whinney Banks Youth & Community Centre
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Anh 
