The men's basketball team were the 2005-2006 Summit Athletic Conference Champions and star guard Eshaunte "Bear" Jones was an Indiana Junior All-Star. The following season, Jones was an Indiana Senior All-Star, wearing #10 in a pair of wins over Kentucky in the state's annual games. In 2008, Justin Jordan was an Indiana Junior All-Star before becoming an Indiana Senior All-Star in 2009. In 2010, an unlikely Redskin team, with a losing record, topped Marion to win Class 4A Sectional #6 for its first Sectional title since 2005.
The men's cross country team has won awards including the SAC (Summit Athletic Conference) Championship in 2008. It qualified for the Indiana State finals competition in 2008 in Terre Haute; the first time since 1969 that the Redskins qualified in cross country.
North Side's marching band, the North Side Marching Redskins, was founded in the 1920s. It placed ninth in the ISSMA State finals competition in 2011, competing in ISSMA class B.
North Side's Football won the SAC for the year 2013-2014. The boys basketball team followed up the SAC winning football team by winning the 2013-2014 SAC regular season and tournament titles. Their back to back regular season conference titles were the first for the school in 35 years and were part of a state best 18-1 start to the 2013-2014 season. The 2014-2015 boys basketball would again win the regular season SAC title, their third in a row under coach Shabaz Khaliq.