| Season | Bowling_Stats | Player | Fixture |
| 1897 | 7-37 | A. Simpson | Stockton v Guisborough |
| 1898 | 7-49 | A. Branson | Thornaby v Stockton |
| 1899 | 8-21 | W. Bootham | Stockton v Redcar |
| 1900 | 10-50 | T. Wales | Stockton v Norton |
| 1901 | 8-24 | A. Hall | Norton v West Hartlepool |
| 1902 | 9-16 | A. Hall | Norton v North Ormesby |
| 1903 | 8-42 | A. Dennis | Middlesbrough v Thornaby |
| 1904 | 10-70 | S. Dixon | Redcar v Norton |
| 1905 | 9-63 | C.P. Barrowcliff | Stockton v West Hartlepool |
| 1906 | 9-62 | R. Williams | Guisborough v West Hartlepool |
| 1907 | 9-32 | J.H. Featherstone | Redcar v Stockton |
| 1907 | 9-32 | T. Gale | Guisborough v West Hartlepool |
| 1908 | 9-44 | E. Thompson | North Ormesby v Norton |
| 1909 | 9-17 | F.J. Horsley | Seaton Carew v Thornaby |
| 1910 | 9-45 | A. Dennis | Middlesbrough v North Ormesby |
| 1911 | 10-35 | F. Sanderson | Guisborough v Norton |
| 1912 | 8-13 | J.G. Chipchase | Darlington v Norton |
| 1913 | 8-25 | K. Thompson | North Ormesby v Saltburn |
| 1915 | | Great War | |
| 1916 | | Great War | |
| 1917 | | Great War | |
| 1918 | | Great War | |
| 1919 | | Great War | |
| 1920 | 8-14 | E. Vincent | Norton v Stockton |
| 1921 | 9-18 | W. Gilbert | Stockton v Saltburn |
| 1922 | 10-61 | W. Gilbert | Stockton v Saltburn |
| 1923 | 9-14 | S. Dickson | Preston v Saltburn |
| 1924 | 10-27 | V. Dodd | Middlesbrough v Norton |
| 1925 | 9-40 | J.A. Close | Bishop Auckland v West Hartlepool |
| 1926 | 9-13 | H. Wright | Stockton v Redcar |
| 1927 | 10-7 | W. Phillips | Saltburn v Normanby Hall |
| 1928 | 9-26 | R. MacKay | Darlington RA v Preston |
| 1929 | 9-44 | W. Gilbert | Stockton v Redcar |
| 1930 | 9-41 | W.S. Smith | Saltburn v Stockton |
| 1931 | 9-88 | E. Watson | Preston v Guisborough |
| 1932 | 9-53 | S. Smith | Darlington RA v Darlington |
| 1933 | 8-28 | J.C. Foster | Middlesbrough v Billingham Synthonia |
| 1934 | 8-39 | H.D. Chapman | Guisborough v Preston |
| 1935 | 9-27 | L. Harris | Blackhall v Yarm |
| 1936 | 10-27 | W.S. Smith | Saltburn v Normanby Hall |
| 1937 | 9-21 | R.W. Hamilton | Bishop Auckland v Darlington RA |
| 1938 | 9-23 | F. Garmonsway | Bishop Auckland v Guisborough |
| 1939 | 9-38 | A. Graham | Normanby Hall v Yarm |
| 1940 | | No Competition | |
| 1941 | 10-33 | W. Green | Middlesbrough v Stockton |
| 1942 | 8-63 | J. Bonnor | Stockton v Thornaby |
| 1943 | 8-21 | H. Wilkie | Summersons v Stockton |
| 1944 | 8-11 | C. Lindridge | West Hartlepool v Norton |
| 1945 | 8-6 | H. Prout | Normanby Hall v Billingham Synthonia |
| 1946 | 9-15 | H.T. Brodie | Preston v West Hartlepool |
| 1947 | 10-37 | H.T. Brodie | Preston v Great Ayton |
| 1948 | 10-27 | J.R. Thomas | Billingham Synthonia v Normanby Hall |
| 1949 | 8-23 | A. Middlemiss | Normanby Hall v Darlington RA |
| 1950 | 9-39 | N. Hudson | Saltburn v Redcar |
| 1951 | 9-32 | C. Spencer | Guisborough v Billingham Synthonia |
| 1952 | 8-10 | K. Pooley | Middlesbrough v Bishop Auckland |
| 1953 | 9-41 | R. Walker | West Hartlepool v Saltburn |
| 1954 | 10-42 | N. Nevison | Thornaby v Yarm |
| 1955 | 9-70 | T.H. Pratt | Darlington v Preston |
| 1956 | 9-37 | F. Coppack | Yarm v Great Ayton |
| 1957 | 8-24 | D. Tanfield | Great Ayton v Middlesbrough |
| 1958 | 10-19 | N. Watson | Darlington v Darlington RA |
| 1959 | 10-53 | A. English | Marton v Bishop Auckland |
| 1960 | 9-3 | R. Davidson | Bishop Auckland v West Hartlepool |
| 1961 | 9-61 | B. Gratton | Guisborough v Blackhall |
| 1962 | 8-20 | P. Cook | Stokesley v Yarm |
| 1963 | 8-17 | G. Mason | Billingham Synthonia v Bishop Auckland |
| 1964 | 8-20 | R. Walker | Marske v Yarm |
| 1965 | 9-35 | J. Glaister | Bishop Auckland v Normanby Hall |
| 1966 | 9-52 | N. Wilson | Darlington RA v Stockton |
| 1967 | 8-30 | N. Taylor | Billingham Synthonia v Saltburn |
| 1968 | 9-34 | B. Pawson | Marton v Hartlepool |
| 1969 | 8-20 | J. Rodgers | Darlington RA v Guisborough |
| 1970 | 9-24 | R. Walker | Marske v Hartlepool |
| 1971 | 8-19 | B. Jeffels | Stockton v Redcar |
| 1972 | 9-18 | C.W. West | Stokesley v Normanby Hall |
| 1973 | 8-19 | B. Jeffels | Stockton v Great Ayton |
| 1974 | 9-24 | R. Smith | Guisborough v Billingham Synthonia |
| 1975 | 9-34 | F. Young | Blackhall v Hartlepool |
| 1976 | 8-21 | C. Beeforth | Middlesbrough v Thornaby |
| 1977 | 8-16 | I. Russell | Great Ayton v Bishop Auckland |
| 1978 | 10-8 | I. Russell | Great Ayton v Stockton |
| 1979 | 10-16 | A. Dennison | Marton v Billingham Synthonia |
| 1980 | 9-17 | D. Blackett | Barnard Castle v Castle Eden |
| 1981 | 9-30 | R. Cawson | Hartlepool v Guisborough |
| 1982 | 10-54 | R. Darwin | Richmondshire v Northallerton |
| 1983 | 10-39 | D. Clements | Guisborough v Saltburn |
| 1984 | 9-24 | B. Wain | Nunthorpe v Blackhall |
| 1985 | 8-33 | M. McCabe | Redcar v Yarm |
| 1986 | 9-28 | M. Mitchinson | Stockton v Normanby Hall |
| 1987 | 8-25 | B. Wain | Nunthorpe v Blackhall |
| 1988 | 9-40 | S.H. Smith | Hartlepool v Saltburn |
| 1989 | 8-13 | D.P. Foster | Marton v Billingham Synthonia |
| 1990 | 8-21 | M. Newlove | Seaton Carew v Yarm |
| 1991 | 9-45 | R. Eastwood | Nunthorpe v Stokesley |
| 1992 | 8-31 | J. Pybus | Northallerton v Saltburn |