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In January 2019, despite only playing 3 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. 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. 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.

As a youth Annesley spent time with both AFC Wimbledon and Chelsea. Annesley started his senior career at non-league side Cobham, breaking into the senior side and making 10 appearances in his only season at the club in the Combined Counties Football League. This attracted the attention of Barnet, who signed him to their academy in 2017. He left in early 2018, signing for Gibraltar Premier Division champions Lincoln Red Imps in July 2018. He made his debut on 26 July 2018 in the UEFA Europa League first leg against The New Saints.

In March 2018, he made his debut for the Gibraltar national football team, 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.

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. Later that year, he made his debut for the under-17 side, with whom he earned 5 caps. In 2016, he played 3 games for the Gibraltar national under-19 football team before earning a callup for the first Gibraltar national under-21 football team in 2017, with whom he has 8 caps to date. Annesley notably made a late goal-line clearance in Gibraltar U21s' 1–0 victory over Macedonia.

Louie John Annesley (born 3 May 2000) is a British footballer who currently plays as a centre-back for Blackburn Rovers in the EFL Championship. Born in London, he represents the Gibraltar national football team at international level.