Mens Premierships
Since its establishment in August 1909, Bentleigh Cricket Club have won 48 mens premierships including six (6) VJCA / VTCA Senior Division Premierships; making the Club the most successful in the VJCA / VTCA to date.
| Season | Grade / Division | Team | Association | Opponent |
| 1909 - 10 | A Grade | 1st XI | Caulfield-Moorabbin Association | |
| 1910 - 11 | A Grade | 1st XI | Caulfield-Moorabbin Association | |
| 1911 - 12 | A Grade | 1st XI | Caulfield-Moorabbin Association | |
| 1912 - 13 | A Grade | 1st XI | Caulfield-Moorabbin Association | |
| 1913 - 14 | Brighton District Association | |||
| 1917 - 18 | Brighton District Association | |||
| 1931 - 32 | A Grade | 1st XI | Moorabbin & District Cricket Association | Bentleigh ANA |
| 1932 - 33 | A Grade | 1st XI | Moorabbin & District Cricket Association | Bentleigh ANA |
| 1933 - 34 | A Grade | 1st XI | Moorabbin & District Cricket Association | G.U.O.O.F. |
| 1936 - 37 | A Grade | 1st XI | Bentleigh & District Cricket Association | H.A.C.B.S. |
| 1938 - 39 | A Grade | 1st XI | Bentleigh & District Cricket Association | M.U.I.O.O.F. |
| 1939 - 40 | A Grade | 1st XI | Bentleigh & District Cricket Association | M.U.I.O.O.F. |
| 1941 - 42 | A Grade | 1st XI | Bentleigh & District Cricket Association | Bentleigh ANA |
| 1943 - 44 | A Grade | 1st XI | Bentleigh & District Cricket Association | Sherwood |
| 1945 - 46 | A Grade | 1st XI | Bentleigh & District Cricket Association | Brighton Union |
| 1946 - 47 | A Grade | 1st XI | Bentleigh & District Cricket Association | Bentleigh ANA |
| 1946 - 47 | C Grade | 3rd XI | Bentleigh & District Cricket Association | Glenhuntly |
| 1947 - 48 | A Grade | 1st XI | City of Moorabbin Cricket Association | Highett No 1 |
| 1947 - 48 | C Grade | 3rd XI | City of Moorabbin Cricket Association | Deutscher |
| 1948 - 49 | A Grade | 2nd XI | City of Moorabbin Cricket Association | Bentleigh Methodist |
| 1952 - 53 | South A2 | 2nd XI | Victorian Junior Cricket Association | Carnegie |
| 1954 - 55 | South A1 | 1st XI | Victorian Junior Cricket Association | Moorabbin |
| 1957 - 58 | South A2 | 2nd XI | Victorian Junior Cricket Association | Carnegie |
| 1960 - 61 | C Grade | 3rd XI | City of Moorabbin Cricket Association | South Oakleigh Methodist |
| 1966 - 67 | South A1 | 1st XI | Victorian Junior Cricket Association | Frankston |
| 1968 - 69 | Senior Division | 1st XI | Victorian Junior Cricket Association | Flemington - Kensington |
| 1975 - 76 | Senior Division | 1st XI | Victorian Junior Cricket Association | McKinnon |
| 1976 - 77 | Senior Division | 1st XI | Victorian Junior Cricket Association | South Caulfield |
| 1978 - 79 | South D | 4th XI | Victorian Junior Cricket Association | Oakleigh |
| 1978 - 79 | J Grade | 5th XI | City of Moorabbin Cricket Association | Heatherton |
| 1979 - 80 | I Grade | 5th XI | City of Moorabbin Cricket Association | St Kilda City |
| 1983 - 84 | Senior Seconds | 2nd XI | Victorian Junior Cricket Association | East Malvern |
| 1984 - 85 | Senior Division | 1st XI | Victorian Junior Cricket Association | Royal Park - Brunswick |
| 1986 - 87 | South C | 3rd XI | Victorian Junior Cricket Association | Brighton East |
| 1987 - 88 | J Grade | 5th XI | City of Moorabbin Cricket Association | South Caulfield |
| 1988 - 89 | South A | 1st XI | Victorian Junior Cricket Association | Highett |
| 1989 - 90 | South C | 3rd XI | Victorian Junior Cricket Association | Heatherton |
| 1990 - 91 | Senior Seconds | 2nd XI | Victorian Junior Cricket Association | South Caulfield |
| 1992 - 93 | Senior Division | 1st XI | Victorian Junior Cricket Association | Seddon |
| 1994 - 95 | Senior Seconds | 2nd XI | Victorian Turf Cricket Association | Royal Park - Brunswick |
| 1995 - 96 | J Grade | 5th XI | City of Moorabbin Cricket Association | Moorabbin Park |
| 1999 - 2000 | Senior Division | 1st XI | Victorian Turf Cricket Association | Old Paradians |
| 1999 - 2000 | South D1 | 3rd XI | Victorian Turf Cricket Association | Cheltenham |
| 2006 - 07 | South A1 | 1st XI | Victorian Turf Cricket Association | Murrumbeena |
| 2007 - 08 | C Grade | 3rd XI | Mercantile Cricket Association | Monash Gryphons |
| 2008 - 09 | C Grade | 4th XI | Mercantile Cricket Association | Burnely |
| 2009 - 10 | South Division | 1st XI | Victorian Turf Cricket Association | Beaumaris |
| 2009 - 10 | South Seconds | 2nd XI | Victorian Turf Cricket Association | Beaumaris |