The loan system allows for youngsters to experience valuable first-team football, and Chelsea have benefited massively from it over the years.
In the current Chelsea squad, the likes of Reece James, Trevoh Chalobah and Levi Colwill all enjoyed impressive loan spells earlier in their careers.
Here is a look at every Blues-owned player currently out on loan…
Player Age Playing at
Mamadou Sarr 19 Strasbourg
Mike Penders 20 Strasbourg
Kendry Paez 18 Strasbourg
Caleb Wiley 20 Watford
Deivid Washington 20 Santos
Marc Guiu 19 Sunderland
Leo Castledine 19 Huddersfield Town
Teddy Sharman-Lowe 22 Bolton Wanderers
Even though Chelsea received loan offers for Estevao Willian, the 18-year-old Brazilian attacker is staying put at Stamford Bridge this season. It looks like the rising star is ready to make an immediate impact in Enzo Maresca’s squad, too.
After a successful loan spell with Strasbourg, Chelsea have added Andrey Santos into their group for the new campaign, which should serve as inspiration for the current youngsters out on loan.
Huddersfield Town players celebrate scoring against Leicester City in the Carabao Cup.
Photo by George Wood/Getty Images
Chelsea loanee Leo Castledine enjoys memorable debut for Huddersfield Town
Leo Castledine, who’s a product of the Chelsea academy, has been loaned out for a second consecutive season.
Last year, the 19-year-old attacking midfielder temporarily moved to League One with Shrewsbury, who suffered relegation. He’s followed that up this summer with a season-long loan switch to Huddersfield Town, who sit top of League One after the opening two rounds of fixtures.
Chelsea changed their mind about selling Castledine this transfer window, so we’ll see how the English playmaker does again in the third tier.
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On Wednesday night, Chelsea loanee Castledine made his Huddersfield debut, coming off the bench in the first round tie of the Carabao Cup at home to Leicester City.
After a 2-2 draw in the 90 minutes, Huddersfield completed a cup upset by beating Championship side Leicester 3-2 in the penalty shootout. Incidentally, on-loan youngster Castledine stepped up for his new club and fired in a powerful low finish to show his nerve.
LCFC: ❌ ✅ ✅#htafc: ❌ ✅ ✅
Leo Castledine fires home a wonderful spot kick 👏
— Huddersfield Town (@htafc) August 13, 2025
View Tweet
Hopefully, Castledine can kick on and enjoy an impressive season in Huddersfield colours.
Back in January 2024, Chelsea legend John Terry raved about Castledine as a young prospect with plenty of potential. He made his one and only senior appearance for the Blues under Mauricio Pochettino in a Carabao Cup match against Middlesbrough, and it feels like a long way back to the current first-team squad.
Leicester City players look on during the penalty shootout against Huddersfield Town in the Carabao Cup.
Photo by George Wood/Getty Images
Leo Castledine to shine for Huddersfield Town in 2025/26 season
Even in his first few minutes for Huddersfield, Castledine looked lively off the bench against Leicester. The way he emphatically took his penalty kick was majorly impressive as well.
Minutes played Accurate passes Chances created Touches Clearances Ground duels won Aerial duels won Match rating
28 10/14 (71%) 1 19 3 1/2 (50%) 2/3 (67%) 6.6
Leo Castledine for Huddersfield Town vs Leicester City via FOTMOB
Speaking via Huddersfield’s official website earlier in August, Terriers manager Lee Grant shared his delight about the Castledine loan transfer. He said: “A player with huge potential and someone whose career I have followed closely, we’re all looking forward to working with Leo and helping him add to his game and contribute to the team this season.”
Castledine was an important player for Shrewsbury last term before an injury cut his loan spell early.
We’re confident that the teenage playmaker, who can play multiple attacking roles, is good enough to thrive for a Huddersfield side that should be chasing promotion.