The Southold boys basketball team will face Pierson in an outbracket Class C playoff game Thursday.
The First Settlers were seeded third in the three-team bracket and will play at 6:15 p.m. against their league rival. The winner advances to play No. 1 The Stony Brook School Monday for the county title.
Southold went 10-8 this season and was 8-6 in League VIII. The First Settlers went 0-2 against Pierson, losing most recently, 57-46, on Feb. 3.
The League VIII champion, Bridgehampton, is a Class D school and will be playing Smithtown Christian for the county title.