The following student-athletes have been named captains of their Winter-season teams:
- Girls Hockey: Lucy Battie and Abby Hyriewicz (Brookline High School) and Sonja Klumpp
- Boys Hockey: Griffin Connolly, Connor Kee
- Boys Gymnastics: Tomer Keren
- Girls Gymnastics: Suzie Kaufmann, Camila Hernandez
- Wrestling: Zach Nislick, AJ Josephson
- Girls Basketball: Hannah Lass, Roni Tamir, Julia Hurwitz
- Boys Basketball: Geoff Gray, Mark Karmiy
- Boys Swimming: Mitchell Arruda, Andrew Shaughnessy, Alex Song
- Girls Swimming: Sophia Autor, Jackie Bussgang, Claire McElduff
- Alpine Ski: Molly Mackler, Jessica Landon, Eli Levine, Aleksandr Marceau
- Nordic Ski: Sam Noymer
- Boys Track: Ben Cooper, Ben Weingart
- Girls Track: Matia Whiting, Katherine Cullen, Yuriko Fukumura, Caroline Delheim
