All Upper School wrestlers train together throughout the winter in the Ostrye Wrestling Gymnasium, where a number of plaques and banners adorn the walls as a testament to the hard work and success of past Brunswick teams.
 
Legendary head coach Tim Ostrye currently stands as the winningest coach in New England (NEPSWA) prep school wrestling history with well over 600 wins. The National Prep Wrestling board has honored Ostrye as Head Coach of the Year (2019) and with the Neil Buckley Outstanding Service Award (2006).

Brunswick has won 35 out of the last 41 FAA league championships, including a run of 22 straight from 1998-2019. Bruins teams have won 15 Western New England (WNEPSWA) crowns while picking up countless individual honors and awards in the process. Several Brunswick wrestlers in recent years have earned All-American status at the National Prep Tournament.