Oak Park Raiders History

École Secondaire Oak Park High School has stood in Charleswood since the mid-1970s. The football programme is younger than the school: it started in 1991, in the Winnipeg High School Football League, against opponents who had been playing for decades. Thirty-five seasons later it has sent more players to professional football than any other high school in the country.

What follows is the club’s own record. Where a claim comes from somewhere else, it says so at the bottom of the page.

The first Raiders sides wore blue, white and silver and had no history to draw on. The nineties were spent building one — learning the league, finding coaches, and establishing that a new school in Charleswood intended to be taken seriously.

Records from that first decade are thin, and the club would like them to be less so. If you played in those years, the alumni form is the fastest way to put your season back on the record.

Stu Nixon began coaching in 1987 and spent more than two decades running Oak Park football. He was an assistant on the 2002 provincial championship team and then head coach, and the record under him is the reason the programme is known outside Winnipeg.

Four provincial championships, four finals, and a junior varsity title in 2017 — the list is below. He credited a coaching staff that stayed: Ryan Soroka, Dave Black and Chris Ollson among them, which is why the standards survived each graduating class.

Nixon retired from coaching in 2022 and was inducted into the Manitoba Football Hall of Fame in 2023. He died in May 2025. Brady Oliveira called him a father figure, and that was the common note in what his players said afterwards rather than an unusual one.

Varsity champions in 2002 — Nixon an assistant that year — then 2007, 2010, 2014 and 2025, with finals lost in 2004, 2009, 2011 and 2024. The junior varsity has won four: 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 year running the JV had reached it and the first of those four they won.

The programme 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 — had both come through this school, which is a strange thing to be able to say about one high school in Charleswood.

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

They come back. That is the part the club values most, and it is the reason the alumni section of this site exists rather than being a list of names.

Chris Ollson played here and coached here under Nixon before taking over, and the programme did not dip.

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 opens on 3 September away to Vincent Massey. Every fixture and result on this site comes from the league’s own feed, so the schedule page is current rather than remembered.

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 Pembina Trails School Division’s record of his Manitoba Football Hall of Fame induction. The ten CFL champions figure is CityNews Winnipeg, November 2024. The 2017 junior varsity final and the earlier JV titles are Global News. Everything about 2023 onward — records, scores, playoff rounds — is the league’s own feed, which is where this site’s schedule pages read from as well. The Truth and Reconciliation jerseys, including the quotation, are CBC Manitoba and Pembina Trails, September 2023.

Two things are worth saying plainly. The first is that the pre-2002 decade is thinner here than it should be, and the alumni form is how that gets fixed. The second is that anything on this page that is wrong is worth telling the club about — a history nobody corrects is a history that drifts.