On Friday, October 7, 2016, Cresskill played St. Mary (Ruth.) in Cresskill. In the first quarter, Richard Marques of St. Mary ran the ball one yard to score, with teammate Christopher Butcha kicking the extra point. There was no scoring by Cresskill in this quarter. The second quarter brought about some hope for the Cougars, as senior John Connelly received an 18-yard pass from senior Jack Maltby for a score. Soon after, St. Mary’s Marques scored again by running the ball 11 yards. To counter this, Connelly also scored again after receiving a 49-yard pass from Maltby. Unfortunately, the Cougars were unable to score again and the game ended in a loss, 13-12.