Leo Castledine

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Leo Castledine
Leo Castledine 2022.JPG
Castledine with Chelsea in 2022
Personal information
Full name Leo Alexander Francis Castledine [1]
Date of birth (2005-08-20) 20 August 2005 (age 20)
Place of birth Kingston upon Thames, England [2]
Height 1.79 m (5 ft 10 in) [2]
Position(s)
Team information
Current team
 Middlesbrough
Number 23
Youth career
2011–2013 Chelsea
2013–2020 AFC Wimbledon
2020–2024 Chelsea
Senior career*
YearsTeamApps(Gls)
2024–2026 Chelsea 0 (0)
2024–2025 → Shrewsbury Town (loan) 23 (2)
2025–2026 → Huddersfield Town (loan) 23 (10)
2026– Middlesbrough 0 (0)
International career‡
2019 England U15 6 (0)
2021–2022 England U17 10 (2)
2022–2023 England U18 6 (1)
2023–2024 England U19 5 (2)
* Club domestic league appearances and goals as of 17:10, 9 January 2026 (UTC)
‡ National team caps and goals as of 17:10, 9 January 2026 (UTC)

Leo Alexander Francis Castledine (born 20 August 2005) is an English professional footballer who plays as an attacking midfielder or wide midfielder for EFL Championship club Middlesbrough.

Contents

Club career

Early career

Born in Kingston upon Thames, where he lived only 15 minutes away from the Cobham Training Centre, Castledine started his career with Chelsea, who he had supported growing up. [3] He spent two years with Chelsea before moving to AFC Wimbledon at the age of seven. [3] Growing up, he also played rugby, and was enrolled in the elite academy of professional club Harlequins. [3]

Initially beginning his career with Wimbledon in a more defensive role, he moved up the pitch to operate as a midfielder. [4] Settling into his new role well, he was involved in Wimbledon under-18's pre-season tour of Italy, playing alongside players four years his senior, and went on to make his under-18 debut in 2019 - becoming the youngest Wimbledon player to ever do so. [4]

Chelsea

A year later, in March 2020, he rejoined Chelsea, naming Mason Mount and Jack Grealish as his favourite current players. [4] [5] He signed his first professional contract with The Blues in August 2022, on his seventeenth birthday, and has already been called up to train with the first team. [3] [6]

Castledine made his senior debut for Chelsea as a substitute in a 6–1 EFL Cup semi-final second-leg win over Middlesbrough on 23 January 2024. [7]

Shrewsbury Town (loan)

On 26 August 2024, Castledine joined League One side Shrewsbury Town on a season-long loan deal. [8] [9] He made his debut for the club the next day on 27 August 2024, in a 2–0 defeat to Bolton Wanderers in the EFL Cup. [10] He scored his first goal for the club on 31 August 2024, in a 3–0 win against Leyton Orient. [11]

Huddersfield Town (loan)

On 1 August 2025, he returned to League One, joining Huddersfield Town on a season-long loan. [12] [13] He made his debut for the club on 13 August 2025, in a 2–2 draw with Leicester City in the EFL Cup which Huddersfield won on penalties. [14] He scored his first goal for the club on 26 August 2025, in a 1–1 draw with Sunderland. [15] Having scored five goals in his final month with the club prior to his recall, he was named EFL Young Player of the Month and EFL League One Player of the Month for December 2025. [16] [17]

Middlesbrough

On 9 January 2026, Castledine signed for Championship side Middlesbrough on a four-and-a-half year deal for an undisclosed fee, reported to be a little under £1 million. [18] [19]

International career

Castledine has represented England at under-15, under-17 and under-18 level. [2]

On 15 November 2023, Castledine scored on his England U19 debut during a 6–0 win over Romania in Marbella. [20]

Personal life

He is the son of former Wimbledon footballer, and television presenter, Stewart Castledine, as well as former Homes Under the Hammer host Lucy Alexander. [3] [21] Leo has an older sister, Kitty, an actress who currently stars in EastEnders .

Career statistics

As of match played 4 January 2026 [22]
Appearances and goals by club, season and competition
ClubSeasonLeague FA Cup EFL Cup OtherTotal
DivisionAppsGoalsAppsGoalsAppsGoalsAppsGoalsAppsGoals
Chelsea U21 2022–23 ———5 [a] 050
2023–24 ———3 [a] 030
Total———8080
Chelsea 2023–24 Premier League 000010—10
2024–25 Premier League0000000000
2025–26 Premier League0000000000
Total0000100010
Shrewsbury Town (loan) 2024–25 League One 23210101 [a] 0262
Huddersfield Town (loan) 2025–26 League One231000311 [a] 12712
Middlesbrough 2025–26 Championship 000000—00
Career total461210511016214
  1. 1 2 3 4 Appearances in EFL Trophy

Honours

Individual

References

  1. ↑ "Premier League clubs publish 2022/23 retained lists". www.premierleague.com. Retrieved 6 July 2023.
  2. 1 2 3 Leo Castledine at WorldFootball.net
  3. 1 2 3 4 5 Johnson, Simon (24 November 2022). "Chelsea's 17-year-old midfielder who learned from his Wimbledon dad". theathletic.com. Retrieved 27 December 2022.(subscription required)
  4. 1 2 3 "Leo departs Wimbledon after seven years to join Chelsea". afcwimbledon.co.uk. 13 March 2020. Retrieved 27 December 2022.
  5. ↑ Shalashov, Michail (11 March 2020). "Chelsea new signing Leo Castledine quotes Mount and Villa's Grealish among favourite players". tribuna.com. Retrieved 27 December 2022.
  6. ↑ Kingsley, Igho (21 August 2022). "Talented midfielder reacts to signing new deal with Chelsea". allnigeriasoccer.com. Retrieved 27 December 2022.
  7. ↑ "Match report: Chelsea 6 Middlesbrough 1 (6-2 agg)". chelseafc.com. 23 January 2024. Retrieved 7 February 2024.
  8. ↑ "Leo Castledine Signs For Salop!". Shrewsbury Town F.C. 26 August 2024. Retrieved 10 January 2026.
  9. ↑ "Loan move for Castledine". www.chelseafc.com. Retrieved 27 August 2024.
  10. ↑ "Shrewsbury Town 0–2 Bolton Wanderers". BBC Sport. 27 August 2024. Retrieved 10 January 2026.
  11. ↑ "Shrewsbury Town 3–0 Leyton Orient". BBC Sport. 31 August 2024. Retrieved 10 January 2026.
  12. ↑ "Huddersfield Town make 12th summer signing as Chelsea prospect joins Lee Grant's revolution". Yorkshire Live. 1 August 2025. Retrieved 10 January 2026.
  13. ↑ "LOAN: LEO CASTLEDINE JOINS TOWN". www.htafc.com. 1 August 2025. Retrieved 9 January 2026.
  14. ↑ "Huddersfield Town 2–2 Leicester City". BBC Sport. 13 August 2025. Retrieved 10 January 2026.
  15. ↑ "Sunderland 1–1 Huddersfield Town". BBC Sport. 26 August 2025. Retrieved 10 January 2026.
  16. 1 2 "Sky Bet League One Manager and Player of the Month winners". www.efl.com. 16 January 2026. Retrieved 16 January 2026.
  17. 1 2 "Leo Castledine named EA Sports FC Young Player of the Month". www.efl.com. 19 January 2026. Retrieved 22 January 2026.
  18. ↑ "Leo Castledine Signs From Chelsea". www.mfc.co.uk. 9 January 2026. Retrieved 9 January 2026.
  19. ↑ Johns, Craig (9 January 2026). "Kim Hellberg's Leo Castledine confirmation as he explains Middlesbrough transfer decision". Teesside Live. Retrieved 9 January 2026.
  20. ↑ Smith, Frank (15 November 2023). "Report: England MU19s 6-0 Romania". EnglandFootball.com. Retrieved 16 November 2023.
  21. ↑ "Chelsea sign 14-year-old Leo Castledine from AFC Wimbledon". ghanasoccernet.com. 11 March 2020. Retrieved 27 December 2022.
  22. ↑ Leo Castledine at Soccerway
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