Each year, Upland varsity teams participate in and host a series of regional tournaments, including the Upland Boys' Invitational Ice Hockey Tournament, the oldest junior school ice hockey tournament in the country . These long-standing traditional match-ups are the highlight of every season and eagerly anticipated by students. Here are the trophies Upland teams have brought home in recent years:

Valley School of Ligonier Soccer Tournament
2006-07
2002-03

Valley School of Ligonier Field Hockey Tournament
2006-07
2002-03

Upland Boys Invitational Hockey Tournament
2005-2006
2004-2005

Upland Girls Invitational Ice Hockey Tournament
2006-2007
2005-2006
2003-2004
2002-2003

Upland Boys Lacrosse Tournament
2009-2010
2007-2008
2006-2007
2004-2005

Upland Girls Lacrosse Tournament
2006-2007
2004-2005
2002-2003