Like Perth Amboy, the Carteret Ramblers possess one of the richest histories in Middlesex County Boys Basketball. Carteret has enjoyed at least one 20-win season in six different decades. The Ramblers have compiled 14 seasons with at least 20 victories. Half of those seasons have come in the past 25 years.
| Season | Wins | Losses | Win % |
| 1999-2000 | 26 | 4 | 0.867 |
| 1985-86 | 25 | 3 | 0.893 |
| 2001-02 | 23 | 3 | 0.885 |
| 2017-18 | 23 | 7 | 0.767 |
| 1959-60 | 22 | 4 | 0.846 |
| 1987-88 | 22 | 8 | 0.733 |
| 2000-01 | 21 | 5 | 0.808 |
| 1977-78 | 21 | 5 | 0.808 |
| 2011-12 | 21 | 6 | 0.778 |
| 1982-83 | 21 | 6 | 0.778 |
| 1958-59 | 20 | 4 | 0.833 |
| 1978-79 | 20 | 5 | 0.800 |
| 2019-20 | 20 | 8 | 0.714 |
| 2012-13 | 20 | 8 | 0.714 |