Notable Alumni
Oak Park has sent an unusual number of players into professional football. Three of them played in the same Grey Cup.
Everyone below started at Oak Park. Where a year is marked unconfirmed, it has been worked out from public records rather than the club’s own — the club is checking.
Brady Oliveira
CFL Most Outstanding Player, 2024.
Led the Raiders to the city championship in 2015 and was the WHSFL’s Potter Division offensive player of the year, running for 2,220 yards and 34 touchdowns in his final season. His coach at Oak Park put it more simply: he broke almost every running record there was.
Went to the University of North Dakota and finished as the programme’s seventh all-time rusher. Drafted 14th overall by the Winnipeg Blue Bombers in 2019 — the first running back taken that year — and won Grey Cups in 2019 and 2021. Led the CFL in rushing in both 2023 and 2024, was named the league’s Most Outstanding Canadian in each of those years, and its Most Outstanding Player in 2024.
Nic Demski
Most Valuable Canadian, 108th Grey Cup.
Named the WHSFL’s Potter Division offensive player of the year in 2010, and MVP of the championship game in his final season with the Raiders.
Played four seasons for the University of Manitoba Bisons and became the first Bison named to four straight CIS All-Star teams. Taken sixth overall by the Saskatchewan Roughriders in the 2015 draft before coming home to Winnipeg. Two Grey Cups, in 2019 and 2021, and named the 2021 final’s Most Valuable Canadian. Passed a thousand receiving yards in a season in 2023.
Sean Jamieson
Grey Cup champion, 2023.
Won the WHSFL’s Potter Division MVP award in 2011 — an unusual honour for a lineman, and the league’s own records confirm the year.
Five seasons with the Western Mustangs, twice a First Team All-Canadian. Drafted 20th overall by the Montreal Alouettes in 2016 and spent his whole professional career there, starting at centre. Won the Grey Cup with Montreal in 2023, dressing for the final after missing the entire regular season with a knee injury. Now coaches the offensive line at Western.
More: Wikipedia · WHSFL award records
Charlie Ringland
Threw three touchdowns to win Oak Park the 2017 CTV Cup.
A two-way starter at quarterback and free safety who also returned kicks, and in his final year threw three touchdowns to lead the Raiders to the 2017 WHSFL CTV Cup. He was a Raider off the football field too — he scored the winning goal in Oak Park’s 2016 city hockey championship.
Six seasons with the University of Saskatchewan Huskies, where he was rookie of the year in 2018 and a U Sports All-Canadian in 2022. Drafted by the BC Lions in 2023 and made his professional debut in August 2024; started for the Ottawa Redblacks in 2025.
Andrew Harris
The only Canadian to rush for 10,000 yards in the CFL.
Came to Oak Park for his final year of high school after starting at Grant Park. A short stay, and the club claims it carefully — but he was a Raider, and the club is proud of it.
Four seasons with the Vancouver Island Raiders in junior football, winning three national championships. Signed with the BC Lions in 2009, came home to Winnipeg in 2016 and finished with Toronto. Four Grey Cups as a player — 2011, 2019, 2021 and 2022 — and named the 2019 final’s Most Valuable Player. Led the CFL in rushing three years running and retired with 10,380 career rushing yards, sixth in league history and the only Canadian ever past ten thousand. Signed a one-day contract with the Blue Bombers in 2024 to retire a Bomber.
- Photograph
A long snapper is nearly impossible to photograph well, which is the point of him — the ball already gone and the man upside down. If the club has nothing, a Bisons or Roughriders portrait is fine; this is the one entry where a high school photograph would also settle a factual question, so it is worth asking for.
Cory Huclack
Two Grey Cups, and a job done well by never being noticed.
The club counts Cory Huclack as a Raider, and states plainly that it has not yet found a published record saying so — his professional career is documented in detail and his high school is not named anywhere in it. If you have a team sheet, a yearbook or a clipping that settles it, the club would genuinely like to see it.
Five seasons with the University of Manitoba Bisons from 2002, where he was a Canada West All-Star in both 2005 — a five-interception year — and 2006, a CIS Second Team All-Canadian, and a nominee for the President’s Trophy as the country’s defensive player of the year. He finished among Manitoba’s all-time leaders in both tackles and interceptions. Nobody drafted him: he signed with the Winnipeg Blue Bombers as a free agent in 2007, then spent three seasons with the Montreal Alouettes and four with the Saskatchewan Roughriders, where he handled the long snapping in 55 regular-season games. Two Grey Cups — 2009 with Montreal and 2013 with Saskatchewan — and by the 2010 final he had played in three championship games in four professional seasons. His own description of the job is the best argument for putting him on this page: “If I’m doing my job, nobody should notice me, except downfield making tackles.”
- Photograph
Interior line, so scale and leverage rather than a portrait — 6′4″ and 290lb, and the photograph should say so. A Raiders basketball frame would be a lovely second image if the club has one, because almost nobody expects it.
Cole Adamson
Drafted 38th overall by his hometown team.
Four years a Raider, and the league’s AAA defensive player of the year in 2016 — a season of 54 tackles, nine sacks, two forced fumbles and a blocked kick, and he punted as well. He represented Canada at the International Bowl with the under-19 side — and he was not only a footballer here: he won a provincial championship playing centre for the Oak Park basketball team. Six foot four is useful in both places.
Six seasons with the University of Manitoba Bisons, a Canada West all-star in 2021 and a team captain in his final year, finishing with 91 tackles, 7.5 for loss, an interception and a blocked kick. The Winnipeg Blue Bombers took him in the fourth round of the 2022 draft, 38th overall, and signed him before training camp — a Winnipeg kid drafted by Winnipeg. The Bombers then asked him to cross the line of scrimmage and learn the offensive line from scratch, which he took on rather than resisted: “For defence, it was a lot of fun throwing twists at the linemen, but seeing what they have to handle, it’s something else.”
More: University of Manitoba Bisons · 3DownNation — signed after the 2022 draft · ChrisD.ca — his Oak Park years and 2016 season
- Photograph
The Hardy Cup kick if any frame of it can be licensed — it is the single most famous thing any Oak Park graduate has done on a football field, and it is one image. Otherwise a follow-through, shot low, with the ball already gone.
Niko DiFonte
A 59-yard field goal to win the game — a U Sports record.
Oak Park’s special teams player of the season in 2015, and a provincial-level soccer player as well, which is where a good many of the best kickers come from.
Went straight from Oak Park to the University of Calgary and kicked for the Dinos from 2016. In the 2017 Hardy Cup he won the game with a 59-yard field goal — a U Sports record, and a kick that travelled well beyond Canada on its own. He was an All-Canadian in 2018, converting 24 of 28 attempts, and in 2019 kicked two field goals in the Vanier Cup as Calgary won its fifth national championship. The Toronto Argonauts acquired his rights in May 2020 — and then the pandemic cancelled the CFL season outright, so he never took a regular-season snap. That is a hard way for it to end, and it takes nothing away from the 59 yards.
More: University of Calgary Dinos · Toronto Argonauts — rights acquired, May 2020
Someone missing?
This list is not finished and is not meant to be. If you know a Raider who belongs on it, tell the club.
Contact the club