*Club domestic league appearances and goals, correct as of 17:15, 21 December 2024 (UTC) ‡ National team caps and goals, correct as of 15:58, 15 November 2024 (UTC)
In January 2019, despite only playing three league games for the Red Imps and primarily featuring in their Intermediate League squad, he signed for EFL Championship side Blackburn Rovers on a deal until June 2021, initially to play in their development side.[4] Annesley made his Rovers under-23 debut on 4 February, coming off the bench for the final 18 minutes of his side's 7–1 victory over Leicester City in the Premier League 2.[5] He picked up his first piece of silverware at Rovers on 7 May 2019, when he started in the 2–0 Lancashire Senior Cup final victory over local rivals Burnley.[6] He captained the U23s for the first time on 8 March 2021, also scoring his first goal in a 5–1 win over Southampton B in the Premier League 2.[7] In June 2021, he signed a new two-year contract with the club.[8]
On 29 October 2021, Annesley joined National League side, Woking on loan until 4 December 2021[9] and made his debut a day later, in a 3–2 home victory over Altrincham, playing the full 90 minutes.[10] On 6 December 2021, his loan was extended for a further month until the new year, following five first-team appearances.[11] On 5 January 2022, Annesley's loan was extended once more, this time until the end of the current campaign.[12] On 25 January 2022, during a 1–0 away defeat to Bromley, Annesley was sent off for the first time in his playing career, receiving two yellows in the space of two minutes.[13]
In the 2022–23 season, Annesley was elevated to the first team squad for the first time, being given the number 39 shirt. He made his debut in the Carabao Cup second round tie against Bradford City on 23 August 2022, playing the full game and making a crucial late block to ensure a 2–1 victory for Blackburn.[14]
On 22 November 2022, Annesley rejoined National League side, Barnet on loan until 20 December 2022.[15]
Dundalk
On 10 January 2023, Annesley signed a multi-year contract for League of Ireland Premier Division side Dundalk FC.[16] After registering an assist on his debut against UCD,[17] he scored his first goal for the club on 3 March in the 15th minute of a 5–0 in over St Patrick's Athletic.[18] However, shortly after the game he was taken ill, spending 3 weeks in hospital with before returning to light training in April.[19] The illness was later revealed to be sepsis,[20] and caused him to temporarily lose the ability to walk.[21] In a season heavily disrupted by injury, Annesley played 18 games in total, scoring twice.
On 15 March 2024, Annesley was appointed Dundalk captain for the first time in place of injured captain and vice-captain John Mountney and Andy Boyle, in a 0–0 draw with Waterford.[22] However, after the departure of manager Stephen O'Donnell saw him frozen out of the team, and he eventually left the club in June 2024.
Annesley is the first player to have represented Gibraltar at every level from U16 to senior level, first appearing for the under-16 side in March 2015 while on the books at Chelsea.[citation needed] Later that year, he made his debut for the Gibraltar U17 national team, with whom he earned five caps. In 2016, he played three games for the Gibraltar U19[24] before earning a call up for the first Gibraltar U21 in 2017, with whom he has eight caps to date. Annesley notably made a late goal-line clearance in Gibraltar U21s' 1–0 victory over North Macedonia.
In March 2018, Annesley made his debut for the senior national team,[25] starting at the last minute after an injury to Joseph Chipolina in the warm-up. He was substituted in the second half as they held on for a 1–0 win over Latvia. He earned his second senior cap on 13 October, coming off the bench in another 1–0 victory, this time away at Armenia to win Gibraltar's first competitive points at senior level.[26]
