| Year | Description |
| 1952 | The league is formed by eleven founder members. Stockport Sunday School, New Mills, Compstall, Bredbury St. Marks, Hazel Grove, Dove Holes, Chapel-en-le-Frith, Whaley Bridge, Romiley, Hayfield and Birch Vale. Play start time 2-45PM. An extra 15 minutes play after the normal match finish time was allowed if the game was at a definite stage. 8 Ball overs to be bowled. A League representative side played Herbert Sutcliffe's XI at New Mills. The first league dinner was held on Saturday November 15th, 5 -30 PM Start!!
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| 1953 | Poynton join the league. Match times changed to 2.30PM start in April, 2.15PM Start in September.
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| 1954 | The league representative XI play and beat a South Australia touring team in a game played at New Mills. The first inter league game was played against the High Peak league.
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| 1955 | A Champions versus the Rest of the league game is introduced. 100 League wickets in a season taken for the first time.
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| 1960 | All start times are 2.30 PM. The league representative XI play the Cheshire County League at Chester, and the Derbyshire Colts at Chapel-en-le-Frith for the first time.
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| 1963 | Six Under 17's teams introduced to the league.
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| 1966 | Whit Friday matches are all moved to Whit Monday. Poynton resign from the league.
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| 1967 | Hawk Green join the league.
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| 1968 | Sight screens are made compulsory at each end of the ground. The league representative XI defeat the Cheshire Minor Counties XI.
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| 1969 | The Bissenden Cup was introduced.
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| 1971 | The league representative XI defeat the Cheshire Minor Counties XI.
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| 1972 | The Hawke Trophy was introduced. Overs cricket was also introduced. Teams would play 37 x 8 ball per side. Time lost to rain up to 30 minutes added to the end of the game. Romiley resign from the League.
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| 1973 | Mirrlees join the league.
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| 1975 | The League is expanded to 14 clubs. Woodley and Buxworth join.
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| 1977 | Start times changed to 2.00 PM start, instead of 2.30 PM. All games are now made into 90 x 6 ball overs, 45 per side. Bredbury St. Marks resign from the league.
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| 1978 | Tintwistle join the league.
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| 1980 | The League representative XI reach the last 8 of the National Trophy, but lose in a tied game.
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| 1982 | Mirrlees voted out of the league.
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| 1983 | Old Glossop join the league.
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| 1992 | The league gains sponsorship from VW Links garage of Buxton.
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| 1994 | 1000 League runs scored in a season by an individual.
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| 1996 | George Mullaney dies after 37 years service as Secretary to the league.
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| 1997 | The George Mullaney Cup is inaugurated.
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| 1998 | The Cheshire Pyramid is introduced. All clubs stay loyal to the league.
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| 2000 | The league expands to 24 clubs. 10 New teams are introduced. Newton, Romiley, High Lane, Dinting, Hollingworth, Broadbottom, Charlesworth, Mellor, Mottram and Hadfield St. Andrews. All teams to play each other once in a season. New League sponsors are Meridian Contract Hire.
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| 2001 | The league is expanded to Four divisions.
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| 2002 | Golden Jubilee year.
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| 2006 | New website launched as Peak Sports take over the sponsorship of the league.
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