Part of the $13-million expansion of the Freeman Athletic Center completed in January, 2005, Silloway Gymnasium was named in May, 2006 for alumnus and benefactor Stuart Silloway '29, the first of three generations of Stuart Silloways to attend Wesleyan (Stuart Silloway Jr. '59 and Stuart Silloway III '91 comprising the other two). It has seating for 1,200 spectators, three basket supports at each end and an outstanding scoreboard which provides for player details and a message center. The wooden surface is lined in black for one main basketball court, two side basketball courts lined in yellow and two volleyball courts lined in red.
Silloway Gymnasium also debuted as a wrestling facility for the 2006 New England Wrestling Conference Championships, and the Cardinals hosted the New England Championships again in 2012. Over the years, Silloway Gym has been used consistently, along with Bacon Field House, as the location for wrestling dual matches and tournament activity throughout the season.