What position does Leo Castledine play?

Leo Castledine plays as a cen att mid.

What team does Leo Castledine play for?

Leo Castledine plays for Middlesbrough.

What is Leo Castledine's squad number?

Leo Castledine wears number 19.

Leo Castledine

Leo Castledine of Middlesbrough was born in Kingston upon Thames, England on 20 August 2005 (age 21).

Leo Castledine, born on 20 August 2005 (age 20), is an English central attacking midfielder at Middlesbrough, where he wears the number 23 shirt.

His senior career has been shaped chiefly at Middlesbrough. Across two seasons he has made 10 league appearances and scored one league goal, with his most productive spell coming in 2025-26, when he scored once in nine league games.

In 2026-27, Castledine has featured in the Championship, the League Cup and the Championship play-offs for Middlesbrough, making four appearances across all competitions. His current market value is around £1.5m, according to Transfermarkt.

📈 Key stats and insights

Leo Castledine has made 1 Championship appearance (1 start) in 2026–27

Leo Castledine has 1 League Cup appearance and 2 Championship Play-offs appearances in 2026–27

Leo Castledine joined Middlesbrough for an undisclosed fee in January 2026

Leo Castledine's market value is €2.00m

Last updated 19 August 2026. Send feedback

Leo Castledine stats

Check out all of the statistics about Leo Castledine.

Cen Att Mid
Primary Position: Midfielder
Position

CAM

1.75m (5ft 8in)
Height: 19
Squad Number: 68kg (10st 9lb)
Weight: 20 August 2005 (age 21)
Date of Birth: Kingston upon Thames
Birthplace: England 🏴󠁧󠁢󠁥󠁮󠁧󠁿
Country of Birth: Middlesbrough
Team: £1.5m (via Transfermarkt)
Market Value

📊 Season stats

Team: Middlesbrough
Championship 2026 - 2027
Games: 1
Starting: 1
Substitute: -
Unused: 1
Utilisation: 50%
Goals: -
Yellows: -
Reds: -

Team: Middlesbrough
League Cup 2026 - 2027
Games: 1
Starting: 1
Substitute: -
Unused: -
Utilisation: 100%
Goals: -
Yellows: -
Reds: -

Team: Middlesbrough
Championship Play-offs 2025 - 2026
Games: 2
Starting: -
Substitute: 2
Unused: 1
Utilisation: 67%
Goals: -
Yellows: -
Reds: -

Castledine has made 1 Championship appearance (1 start) in the 2026–27 season, and has appeared once in the League Cup plus twice in Championship Play-offs matches – he has scored 0 goals; the small sample of appearances points to a rotational or developmental role at Middlesbrough rather than a regular starting place.

📋 Career stats

Team: Middlesbrough
Season 2026 - 2027
Country: England 🏴󠁧󠁢󠁥󠁮󠁧󠁿
Games: 1
Goals: -

Team: Middlesbrough
Season 2025 - 2026
Country: England 🏴󠁧󠁢󠁥󠁮󠁧󠁿
Games: 9
Goals: 1

Castledine's career traced a path from joining Chelsea as a trainee in March 2020 to loan spells at Shrewsbury Town in August 2024 and Huddersfield Town in August 2025, before a permanent move to Middlesbrough in January 2026 – a progression from youth setup to a permanent senior-team environment.

💰 Transfers

Team: Middlesbrough
9 January 2026
From: Chelsea
Type: Undisclosed

Team: Huddersfield Town
1 August 2025
From: Chelsea
Type: Loan

Team: Shrewsbury Town
26 August 2024
From: Chelsea
Type: Loan

Team: Chelsea
11 March 2020
Type: Trainee

The transfer record comprises two loan moves followed by a permanent transfer – loans to Shrewsbury Town (August 2024) and Huddersfield Town (August 2025) preceded an undisclosed transfer from Chelsea to Middlesbrough in January 2026 – a clear shift from academy pathway to securing a Championship-level contract.

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🔗 External links

Leo Castledine on Transfermarkt