In 1956-57, fifteen schools in Middlesex County played boys basketball. Over the years and decades that number has grown to twice as many. Below is the list of schools in Middlesex County that have enjoyed the success of 20 wins in a season since 1956-67. Colonia and St. Joseph’s top the list with two dozen 20-win seasons.
| School | 20-Win Seasons |
| Colonia | 24 |
| St. Joseph’s | 24 |
| Perth Amboy | 18 |
| Carteret | 14 |
| St. Peter’s | 14 |
| New Brunswick | 13 |
| Piscataway | 11 |
| South Brunswick | 11 |
| Cardinal McCarrick / St. Mary’s (S.A.) | 11 |
| South Plainfield | 10 |
| Woodbridge | 9 |
| East Brunswick | 9 |
| South River | 8 |
| Sayreville | 8 |
| North Brunswick | 7 |
| Piscataway Tech | 6 |
| Metuchen | 6 |
| Spotswood | 5 |
| St. Thomas Aquinas | 5 |
| Timothy Christian | 5 |
| Wardlaw-Hartridge | 4 |
| Monroe | 4 |
| J.F. Kennedy | 4 |
| Perth Amboy Tech | 3 |
| Middlesex | 3 |
| J.P. Stevens | 3 |
| Highland Park | 3 |
| Dunellen | 3 |
| South Amboy/Hoffman | 2 |
| Old Bridge/Cedar Ridge/Madison Township | 2 |