The Dineley Shield was played for from 1963 to 1995. It was presented to the league by Councillor A. Rowland Dineley J.P., who was chairman of the Cheadle and Gatley Urban District Council in 1958/59. The winners were as follows.
| 1963 | Greyhound Hotel |
| 1964 | Royal Oak |
| 1965 | Fletcher Moss Park |
| 1966 | Cheadle Conservative |
| 1967 | Simon Carves |
| 1968 | Simon Carves |
| 1969 | Farmers Arms |
| 1970 | Simon Carves |
| 1971 | Cheadle Heath A |
| 1972 | Fletcher Moss |
| 1973 | Cheadle Heath A |
| 1974 | Fletcher Moss |
| 1975 | Cheadle Heath Social Club |
| 1976 | Driver Harris |
| 1977 | Driver Harris |
| 1978 | Bramhall Queensgate |
| 1979 | Heaton Mersey Cons A |
| 1980 | Heaton Mersey Conservative |
| 1981 | High Lane Conservative |
| 1982 | Simon Carves |
| 1983 | Waggon and Horses |
| 1984 | Albert Club |
| 1985 | Bramhall Park A |
| 1986 | Europa House |
| 1987 | Gatley Recreation |
| 1988 | Levenshulme Catholic |
| 1989 | Albert Club |
| 1990 | Cheadle Conservative |
| 1991 | Bungalow |
| 1992 | Waggon and Horses |
| 1993 | Albert Club |
| 1994 | Albert Club |
| 1995 | Bungalow A |
In 1996, the Dineley Shield was replaced by the Bob Newlan Memorial Trophy. This trophy was bought by the league to commemorate Bob Newlan who was secretary up to 1994. The winners of this trophy are as follows.