Everton After playing with Crosby Stuart, Connolly joined
Everton at the age of nine. He has earned representation at
England under-17 and
under-18 level. On 3 March 2016, he joined
League One side
Barnsley on a one-month loan deal. He made his debut two days later, in a 3–1 win over
Walsall at the
Bescot Stadium. Connolly made his first Everton teamsheet on 16 April 2016, when he was named as a substitute for the 1–1 draw with Southampton, coming on as a second-half substitute for injured right-back
Seamus Coleman to make his Premier League debut. On 14 January 2017, Connolly signed on loan for
Wigan Athletic until the end of the season, and just hours later made his debut and scored both goals as Wigan beat
Burton Albion 2–0. For the 2017–2018 season, Connolly played on loan for
Ipswich Town in the
EFL Championship. Used largely in central midfield for the first time in his career, Connolly returned to Everton at the end of the season, having played an impressive 36 matches, scoring four goals. At the beginning of the
2018–19 season Connolly re-joined
Wigan Athletic on loan, initially for the whole of the season but on 31 January 2019 he was recalled by Everton and sent on loan for the second half of the season to
Bolton Wanderers On 29 August 2019, Connolly headed out on loan once more, this time joining
League One side
Lincoln City on a season-long deal, but he returned to Everton early, after his loan spell was cut short in January. Connolly signed with
Fleetwood Town on 6 January 2020 on a loan deal for the rest of the 2019–20 season. At the end of the
2020–21 it was announced that Connolly would leave the club at the end of his contract.
Blackpool Connolly signed for Blackpool in July 2021 after becoming a free agent. On 7 May 2024, the club announced he would be leaving the club in the summer once his contract expired.
Stockport County On 15 June 2024, Connolly agreed to join newly-promoted
League One side
Stockport County on a two-year deal on 1 July 2024 after the expiry of his contract at Blackpool. ==International career==