The Pirates kicked off their season in Marianna, FL in the Chipola Classic. On Saturday, the Pirates squared off with Southwest Mississippi from Summit, MS. After going back and forth early in the game PSC went into halftime with an eight-point advantage. The second half was more of the same as the Pirates held on to win the game 79-68. Isaiah Sutherland led Pensacola in scoring with 16 points while Jalen Keago added 13 and Dylan Colon contributed 12. Brendan Terry recorded a double-double with 12 rebounds and 11 points. 

The Pirates made the drive back down I-10 on Sunday this time for a date with the Wolves from Copiah-Lincoln in Mendenhall, MS. Pensacola jumped out to a quick 20-9 advantage but give credit to Copiah-Lincoln as they battled back and cut the deficit to just three at halftime. The second half was a hard-fought slugfest with the Pirates eventually coming out on top 66-63. Jalen Keago led the Pirates in scoring with 16 points while Elijah Wyche and Brendan Terry both chipped in 15 each.