[1][2] Originally hailing from the west Gippsland town of Trafalgar, Connolly began playing with the Moe Football Club in 2016, before joining the Gippsland Power in the NAB League, where he became known for his dashing run off half-back and good kicking.

[3][4] Connolly was not able to make his debut in 2020, and in a Covid-interrupted season was largely relegated to playing scratch matches with the cancellation of the VFL following the outbreak of the pandemic.

This made it difficult for Connolly to break into the senior side, who went on to make the Semi Final that year.

Connolly ultimately replaced Coffield on-field and gained 11 disposals in his first quarter of football.

[2] Following an impressive debut, Connolly retained his place in the team for seven consecutive matches before a concussion sustained in Round 21 saw him miss the final two games of the year.