Chester first achieved success in 2007 when he won the BC juvenile boys' championship.[3] Later on in juniors, he represented British Columbia at two Canadian Junior Curling Championships in 2012 and 2013. In 2012, his team, led by Josh Hozack, finished at the bottom of the standings with a 1–11 record, defeating Newfoundland and Labrador in their sole victory.[4] The following year, his rink, now skipped by Tyler Klymchuk, qualified for the championship round and finished in seventh with a 4–6 record.[5] Also, while attending the University of Victoria, Chester skipped the Victoria Vikes to a bronze medal at the 2016 CIS/CCA Curling Championships.[6]
From 2015 to 2018, Chester played second on the Glen Jackson rink which also included Andrew Komlodi and Joel Cave. After qualifying for the 2016 Canadian Direct Insurance BC Men's Curling Championship through the final qualification event, the team went 5–2 through the triple knockout, advancing to the playoff round.[9] They then lost 5–2 to Dean Joanisse in the 3 vs. 4 game, eliminating them from contention.[10] The following season, Team Jackson again had a strong provincial run, this time reaching the semifinals where they were again eliminated by Team Joanisse, settling for third.[11] In their final season together, they were eliminated by the Joanisse rink for a third time in the C qualifier of the 2018 belairdirect BC Men's Curling Championship.[12]
Chester reunited with his junior skip Tyler Klymchuk after parting ways with Team Jackson. This arrangement only lasted one season, however, with Chester then joining the Jeff Richard rink for the 2019–20 season. This proved to be the correct move as Team Richard reached the final of the Kelowna Double Cash, the semifinals of the King Cash Spiel and Prestige Hotels & Resorts Curling Classic and the quarterfinals of the Red Deer Curling Classic.[13] At the provincial championship, the team started with two straight wins before losing their next three games to be eliminated.
After the COVID-19 pandemic cancelled the majority of the 2020–21 season, Chester joined the Paul Cseke rink for the 2021–22 season. This team had some tour success, reaching two semifinals in Kelowna and Maple Ridge.[14] In the new year, the team played in the 2022 BC Men's Curling Championship where they defeated the higher ranked Jim Cotter and Tyler Tardi rinks to become the A qualifier.[15] This qualified them for the 1 vs. 2 game where they beat Chester's former skip Jeff Richard. Facing Richard again in the final, the Cseke rink lost their first and only game of the week, giving up three in an extra end to lose 11–8.[16] Despite this, Chester still got to participate in the 2022 Tim Hortons Brier as alternate for Team Richard, his first appearance at the Canadian men's championship. There, Team BC finished fifth in their pool with a 4–4 record.[17] Chester continued playing with Cseke for the next two seasons, however, they never attained the same level of success as in 2022, missing the playoffs at the provincial championship in both 2023 and 2024.
To begin the 2023–24 season, Reese-Hansen and Chester won the Victoria Mixed Doubles Cash Spiel and reached the semifinals of the Chilliwack Championship.[22] Chester then paired with Hannah Durrant to reach the semifinals of the Parksville Double Doubles Spiel before reuniting with Reese-Hansen to reach the final of the first Alberta Curling Series doubles event.[23] In December, the duo won their first mixed doubles provincial as a team, downing Gabby Brissette and Sterling Middleton 10–2 in the championship game.[24] This sent them to the 2024 Canadian Mixed Doubles Curling Championship where they topped their pool with a 6–1 record, earning a direct bye into the quarterfinal round.[25] They then lost 7–5 to Madison and Rylan Kleiter, eliminating them from contention.[26] The following season, Chester won in Victoria with Mahra Harris and in Parksville with Reese-Hansen, giving him two more tour titles. Despite not winning one of the direct-entry berths into the 2025 Canadian Mixed Doubles Curling Olympic Trials, Reese-Hansen and Chester qualified for the Trials as the third highest ranked team on the points standings that was not already qualified.[27]
