Oak Park Raiders History

École Secondaire Oak Park High School has stood in Charleswood since the mid-1970s. Its football program began in 1991, when the Raiders joined the Winnipeg High School Football League against opponents who had been playing for decades. Thirty-five seasons later, Oak Park has sent more players to professional football than any other high school in Canada.

The first Raiders teams wore blue, white and silver. Through the 1990s the program learned the league, found its coaches, and made clear that a new school in Charleswood intended to be taken seriously.

Played for the Raiders in the 1990s? Join the alumni and help fill in the record of those early seasons.

Stu Nixon began coaching in 1987 and led Oak Park football for more than two decades. He was an assistant on the 2002 provincial championship team before taking over as head coach, and his teams made the program known well beyond Winnipeg.

His record includes four provincial championships, four more finals, and a junior varsity title in 2017. He always credited a coaching staff that stayed together — Ryan Soroka, Dave Black and Chris Ollson among them.

Nixon retired from coaching in 2022 and was inducted into the Manitoba Football Hall of Fame in 2023. He died in May 2025. Many of his former players, Brady Oliveira among them, remembered him as a father figure.

Oak Park’s varsity teams won championships in 2002, 2007, 2010, 2014 and 2025, and reached the final in 2004, 2009, 2011 and 2024. The junior varsity won titles in 2010, 2012, 2017 and 2025, and were finalists in 2016, 2020, 2023 and 2024.

The 2017 junior varsity final was a 44–6 win over St Paul’s at Investors Group Field — the fourth straight year the JV had reached the final, and the first of those four they won.

Oak Park has produced ten CFL champions. In the 2024 Grey Cup, two of the Winnipeg Blue Bombers’ most-used offensive players — Brady Oliveira and Nic Demski — were Oak Park graduates.

Andrew Harris took the Raiders to the 2004 final and went on to be a Grey Cup MVP. Sean Jamieson has played professionally on the offensive line. Charlie Ringland played quarterback and free safety here, went on to the Saskatchewan Huskies, was drafted in 2023 and played for the Ottawa REDBLACKS. Their stories are on Notable Alumni.

Many of them come back. Head coach Chris Ollson played here, and Charlie Ringland is now on the varsity coaching staff.

Chris Ollson played for Oak Park and coached under Nixon before becoming head coach in 2022, and the program has kept winning.

In 2024 the varsity side went through the regular season 7–0 and did not concede a single point — 346 scored, none allowed — before losing the final to Dakota. The junior varsity lost their final to Dakota too, 39–33.

In 2025 both sides went back and won. The junior varsity beat Dakota 48–21 on 22 October and finished the season unbeaten at 8–0; the varsity beat Dakota 22–17 in the Anavets Bowl two days later, ending 9–1. Two years earlier the varsity had lost a semi-final to the same club by a single point.

The 2026 season opened on 3 September. Every fixture and result for both squads is on the schedule page.

Of the four biggest schools in Pembina Trails, Oak Park has the highest proportion of students who identify as Indigenous. In 2023 the Raiders played the day before the National Day for Truth and Reconciliation in jerseys their own players had designed.

The idea came from Dawson Andrews, of Dakota Tipi First Nation, who had been given the Manitoba Indigenous Youth Achievement Award two years earlier. He worked on the design with his teammate Rocco Linklater and educational assistant Jamie Gatta: a red handprint for missing and murdered Indigenous women and girls, an orange one for Every Child Matters, a star blanket in the numbers, and the Raiders name in Cree syllabics.

The northern lights run in a pale wash across the numbers. Chris Ollson described them as “a faint homage to our ancestors … and to the alumni of our program as well.” Andrews’ father gave the pre-game speech and performed the coin toss.

The championship years, the finals and Stu Nixon’s coaching dates are from Pembina Trails School Division’s announcement of his Manitoba Football Hall of Fame induction. The ten CFL champions figure is from CityNews Winnipeg (November 2024). The 2017 junior varsity final and the earlier JV titles are from Global News. Results from 2023 onward are the WHSFL’s own. The Truth and Reconciliation jerseys, including the quotation, are from CBC Manitoba and Pembina Trails School Division (September 2023).

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