This cup was kindly donated by G Jasper Newman and Graham A Newman in April 1972 to replace the District Shield, which was completely filled.
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Chesterfield District Cup Winners Winners 1990 – date
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| 2025 | Old Brampton | ||||
| 2024 | Stonebroom Campanile | 2023 | Alfreton | 2022 | Eckington |
| 2020 | Alfreton | 2019 | Old Brampton | 2018 | Old Whittington |
| 2017 | Old Brampton | 2016 | Old Whittington | 2015 | Old Whittington |
| 2014 |
Old Brampton | 2013 | Old Whittington | 2012 |
Old Brampton |
| 2011 |
Staveley | 2010 | Old Whittington | 2009 |
Old Whittington |
| 2008 |
Old Brampton | 2007 | Staveley | 2006 |
Eckington |
| 2005 |
Old Whittington | 2004 | Old Whittington | 2003 |
Old Whittington |
| 2002 |
Old Whittington | 2001 | Old Brampton | 2000 |
Old Whittington |
| 1999 |
Old Whittington | 1998 | Old Whittington | 1997 |
Old Whittington |
| 1996 |
Old Whittington | 1995 | Old Whittington | 1994 |
Old Whittington |
| 1993 | Old Whittington | 1991 | Old Whittington | 1990 | Dronfield |
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Chesterfield District Shield Winners 1972 – 1989
|
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| 1989 | Old Whittington | 1988 | Old Whittington | 1987 | Creswell |
| 1986 | Old Whittington | 1985 | Old Whittington | 1984 | Bolsover |
| 1983 |
Bolsover | 1982 | Old Whittington | 1981 | Old Whittington |
| 1980 |
Bolsover | 1979 |
Old Whittington | 1978 |
Old Whittington |
| 1977 |
Bolsover | 1976 |
Old Whittington | 1975 |
Old Whittington |
| 1974 |
Bolsover | 1973 |
Old Whittington | 1972 |
Old Whittington |