[10] They qualified for the 2019 Manitoba Scotties Tournament of Hearts through the Winnipeg region and surprised many with a strong 5–2 record in the round robin.

After their great run through the 2019 event, the team could not replicate their success at the 2020 Manitoba Scotties Tournament of Hearts, failing to qualify for the playoffs following a 3–2 record.

[15] Due to the COVID-19 pandemic in Canada, the qualification process for the 2021 Canadian Olympic Curling Trials had to be modified to qualify enough teams for the championship.

[18] They also had deep runs at the Atkins Curling Supplies Classic and the SaskTour Women's Moose Jaw but lost in the semifinals at both events.

At the 2022 Manitoba Scotties Tournament of Hearts, Team Jones qualified for the playoffs after a 6–2 record through the round robin and championship pool.

After a slow start, the team found their footing at the 2022 Western Showdown where they advanced all the way to the final before losing to Silvana Tirinzoni.

[20] The team again qualified at the 2022 Curlers Corner Autumn Gold Curling Classic where they lost in the quarterfinals to Gim Eun-ji.

[27] Despite this, Team Ackland still qualified for the 2023 Scotties Tournament of Hearts as Wild Card #3 thanks to their CTRS points earned throughout the season.

In 2018, Oliver qualified for the 2019 Canadian Mixed Curling Championship in Winnipeg, playing lead on the Manitoba team led by Colin Kurz.

[30] The win qualified the team to represent Canada at the 2019 World Mixed Curling Championship where they dominated through the round robin with a 7–0 record.

In the playoffs, they scored wins over Sweden, Denmark and Norway to qualify for the gold medal game against Germany's Andy Kapp.