On Friday, November 11, 2016, the Cougars traveled to Boonton for the first round of the NJSIAA Group 1 Tournament. In the first quarter, Boonton’s Maleek Awan ran the ball 48 yards to be the first to score. To rival this, the Cougars scored twice in the second quarter. Senior Terence McCabe scored on a three-yard pass from senior Jack Maltby and senior John Connelly scored on 12-yard pass from Maltby. Boonton’s Amaro Anderson scored on an 86-yard kickoff return in this quarter, as well. The third quarter consisted only of Cresskill scoring. McCabe scored on a five-yard pass from Maltby and Connelly scored on a 17-yard pass, also from Maltby. In the fourth quarter, Boonton’s Anderson was the only one to score, which he did by running the ball three yards. Anderson converted all three of his extra-point attempts for Boonton. Junior Yianni Tolos converted two extra-point attempts out of a total of three. The game ended in a Cresskill win, 26-21, and the Cougars advanced to the semifinals.