Cutcliffe is a three-time provincial women's champion, winning the Nova Scotia Scotties Tournament of Hearts in 1985, 1987 and 2017.

These three wins earned those teams the right to represent Nova Scotia at their respective national championships, the Scotties Tournament of Hearts.

At the 1985 Scott Tournament of Hearts, the Jackson-led Nova Scotia rink finished the round robin with an 8–3 record, only to lose in the semifinal.

In 2018, at the Canadian Seniors in Stratford, Ontario, Team Mattatall went 9-1 through the round robin, but lost the final to Saskatchewan's Sherry Anderson in an extra end.

In 2020, Pinkney regained the Nova Scotia Masters title, but cancellation of the Canadian championship in Saint John, NB prevented teams from competing.

On the World Curling Tour, Cutcliffe has won two events as a member of the Mattatall rink, the 2015 Lady Monctonian Invitational Spiel.