The Highland Park Owls have a rich tradition in both football and boys basketball in Middlesex County. From the formation of the Greater Middlesex Conference until the early 2000s, the Owls were a consistent fixture in GMC Blue and Gold Division boys hoops races.
Highland Park led by the likes of NFL standout, L.J. Smith, enjoyed a solid run in the late 1990s highlighted by equaling the best season in school history with a 23-4 mark in 1998-99. The Owls won three straight Central Jersey Group 1 crowns in 1997, 1998, and 1999, and reached the Group 1 State Championship game in 1999.
The 1986-87 squad, coached by Frank Cipot, also finished 23-4, but lost to New Brunswick in the 1987 Central Jersey Group 1 Championship. Highland Park went on to win back-to-back sectional titles in 2001 and 2002, but has not been to a sectional championship game since.
| Season | Wins | Losses | Win % |
| 1998-99 | 23 | 4 | 0.852 |
| 1986-87 | 23 | 4 | 0.852 |
| 1957-58 | 20 | 6 | 0.769 |