Upon taking a position in the Art Department in the North Rockland Central School District in the late 1980´s, Christopher Roff was already figuring a way to change the landscape of the boys basketball program. After serving a few years as a coach at Haverstraw Middle School, Roff ascended the Varsity level in 1990. He won almost instantly. Behind the tandem of Juan Martinez and Pierre Brilliant, Roff guided the Raiders to a 15-win season and a Section I Tournament berth. From that point forward, he made sure that this new-found success would continue.

Roff was instrumental in the development of the entire program. He worked closely with the modified level and made sure to involve local CYO and PAL Leagues in the program´s future. He helped to organize the Don Bosco Summer Basketball league at the Marian Shrine in West Haverstraw. The league began with a high school division, and quickly expanded to include a grammar school group. Pretty soon Red Raider Basketball was back as a force in the RCPSAL and was making waves across Section I.

The team´s record improved each of his first three years culminating with League I-B Championships in 1992 and 1993. The 1993 team was the first to reach the Section I Championships at the historic Westchester County Center. Roff´s 1994-95 team began the season 0-4 and then rattled off a school-record 16 straight wins. Behind Juan Rodriguez´s 22.3ppg and Steven Diaz´s 22.2ppg, they won the RCPSAL and League I-B crowns. Roff also directed the Raiders to League 1-B titles in 2003, 06, 07, 09, 2010 and 2011. In all, Roff´s teams made 6 trips to the Section 1 Tournament at the County Center

After 29 seasons, Coach Roff retired from coaching following the 2015-16 season. He finished as the school´s longest tenured basketball coach and is Rockland´s all-time basketball wins leader with 466. He edges out other great coaches such as Spring Valley´s Lou Kliewe (447), Nyack´s Gary Gray (432), and Albertus Magnus´ Tom Collins (400) for the most victories in Rockland County as a boy´s basketball coach. Roff was named a ¨Coach-of-the-Year¨ 17 times by either League I-B, the RCPSAL, or other officials and media outlets. He was also recognized by Section I three times.

In 2017, Roff was inducted into the New York State Basketball Hall of Fame sponsored by BCANY. He, along with his friend and former Red Raider Girls Basketball Coach Rich Korn, are now enshrined alongside other New York basketball greats at the Cool Insuring Arena in Glens Falls, NY.

For many years, Roff also coached baseball in the District. His baseball teams at Farley Middle would often battle Haverstraw for bragging rights as the best team in Rockland County on the modified level. Later, he coached Freshman and Junior Varsity baseball, Freshman and Junior Varsity football, and was an assistant golf coach.

A Congers native, Roff settled in Stony Point over 35 years ago. He and his wife Susan, raised three boys- all of whom played sports for the Red Raiders. Patrick, a football quarterback, graduated in 2007 and completed his studies at the University of Miami in 2011. Shane played Raider football until 2010 and continued his career at Wagner College until his graduation in 2014. C.J. graduated North Rockland in 2012. He later became a graduate assistant at the University of Maryland, finishing after the 2016 season.