Early career Connolly began his career with
Blackburn Rovers, signing a two-year scholarship contract with the club in June 2018. Despite missing the majority of the
2019–20 season through an injury sustained in October 2019, Connolly had his scholarship extended by a further year being released by the club at the end of the following season. In June 2021, Connolly signed with
Cardiff City. Connolly was retained by the club ahead of the 2022–23 season.
Bristol Rovers On 8 January 2022, Connolly joined
League Two side
Bristol Rovers on loan for the remainder of the
2021–22 season. He made his senior debut later that day in a 2–1
FA Cup third round defeat to
Peterborough United, and his league debut came on 22 January 2022. Connolly scored a first senior goal in a vital match against promotion rivals
Port Vale, turning home an
Antony Evans cross to give Rovers the lead having fallen behind early on, Rovers going on to win 3–1. Connolly's first season in professional football ended in success as Rovers were promoted on the final day of the season, a 7–0 victory moving Bristol Rovers into third place, beating
Northampton Town to automatic promotion on goals scored. in 2022. He re-joined Bristol Rovers on a permanent deal, transferring for an undisclosed sum, in June 2022, signing a three-year contract. On 6 August 2022, Connolly scored his first goal since returning to the club on a permanent basis with the second in a 4–0 thrashing of
Burton Albion. On 27 August 2022, it was revealed that Connolly had suffered a stress fracture in his back that would see him out of action for a 'long period'. On 29 October, Connolly made his return to first-team football as a substitute in a 4–2 defeat at
Derby County. On 31 August 2023, Connolly joined League Two club
Morecambe on loan until the end of the
2023–24 season. He was recalled by his parent club on 3 January 2024.
Crewe Alexandra On 1 August 2024, Connolly joined League Two side
Crewe Alexandra on a two-year deal. He made his debut in the side's league 1–0 defeat away at
Barrow. In January 2025, Connolly suffered a torn hamstring in Crewe's 4–1 win over
Bromley, ruling him out of the first team for a few weeks. He scored his first Crewe goal on 22 November 2025, heading home the final goal in a 3–3 League Two draw against
Chesterfield at
Gresty Road. ==International career==