Chelsea F.C. Development Squad and Academy
Football club
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| 2025 | Moisés Caicedo, an Ecuadorian midfielder, won Chelsea F.C. Player of the Season award. |
| 2025 | Portugal's Pedro Neto wins Chelsea F.C. Player of the Season in a 2-1 victory against Fulham at Craven Cottage in the Premier League |
| May 1 2025 | Reggie Walsh debuts for Chelsea at age 16 in a match against Sweden's Djurgårdens IF. |
| March 13 2025 | Genesis Antwi debuts for Chelsea at age 17 in a match against Denmark's Copenhagen. |
| 2024 | Alfie Gilchrist from England wins Chelsea F.C. Player of the Season award. |
| 2024 | Cole Palmer, an English midfielder, won Chelsea F.C. Player of the Season award. |
| 2024 | Ecuador's Moisés Caicedo wins Chelsea F.C. Player of the Season with a 2-1 win against Bournemouth at Stamford Bridge in the Premier League |
| January 31 2024 | Cesare Casadei made his Chelsea debut at age 21 against Liverpool. |
| January 23 2024 | Leo Castledine makes his Chelsea debut at age 18 against Middlesbrough |
| January 6 2024 | Michael Golding debuts at age 17 for Chelsea against Preston North End. |
| 2023 | Thiago Silva, a Brazilian defender, won Chelsea F.C. Player of the Season award. |
| 2023 | Lewis Hall from England wins Chelsea F.C. Player of the Season award. |
| 2023 | England's Conor Gallagher wins Chelsea F.C. Player of the Season after a 2-1 victory against Crystal Palace in the Premier League |
| 2023 | Chelsea Academy won the U17 Premier League Cup and U18 Premier League - Southern Champions titles. |
| 2022 | No Player of the Season award was given |
| 2022 | Harvey Vale from England wins Chelsea F.C. Player of the Season award. |
| 2022 | Mason Mount wins Chelsea F.C. Player of the Season for the second time. |
| August 6 2022 | Conor Gallagher made his Chelsea debut at age 22 against Everton. |
| 2021 | Tino Livramento from England wins Chelsea F.C. Player of the Season award. |
| 2021 | No Player of the Season award was given |
| 2021 | France's Olivier Giroud wins Chelsea F.C. Player of the Season with a 1-0 victory against Atlético Madrid in the UEFA Champions League |
| August 11 2021 | Trevoh Chalobah debuts at age 22 against Villarreal under manager Thomas Tuchel. |
| 2020 | England's Fikayo Tomori wins Chelsea F.C. Player of the Season after a 5-2 win against Wolverhampton Wanderers in the Premier League |
| 2020 | Mateo Kovačić, a Croatian midfielder, won Chelsea F.C. Player of the Season award. |
| 2020 | No Player of the Season award was given |
| 2019 | Conor Gallagher from England wins Chelsea F.C. Player of the Season award. |
| 2019 | Eden Hazard wins Chelsea F.C. Player of the Season for the fourth time. |
| 2019 | Callum Hudson-Odoi from England won Chelsea F.C. Player of the Season award |
| 2019 | Chelsea Under-21s won their second Premier League 2 championship. |
| August 11 2019 | Mason Mount made his Chelsea debut at age 20 against Manchester United under manager Frank Lampard. |
| 2018 | Reece James from England wins Chelsea F.C. Player of the Season award. |
| 2018 | Willian from Brazil wins Chelsea F.C. Player of the Season for the second time |
| 2018 | N'Golo Kanté, a French midfielder, won Chelsea F.C. Player of the Season award. |
| 2018 | Chelsea Academy won the U18 Premier League - National Champions, U18 Premier League - Southern Champions, and U18 Premier League Cup titles. |
| 2018 | Chelsea Academy completed their fifth consecutive FA Youth Cup title, ending an unprecedented winning streak. |
| January 28 2018 | Callum Hudson-Odoi made his Chelsea debut at age 17 against Newcastle United. |
| 2017 | Eden Hazard wins Chelsea F.C. Player of the Season for the third time. |
| 2017 | Chelsea Academy won both the U18 Premier League - National Champions and U18 Premier League - Southern Champions titles. |
| 2016 | Chelsea Academy won their third consecutive U18 Premier League - Southern Champions title. |
| May 11 2016 | Tammy Abraham made his Chelsea debut at age 18 against Liverpool. |
| 2015 | Eden Hazard wins Chelsea F.C. Player of the Season for the second time. |
| 2015 | Chelsea Academy won their second consecutive UEFA Youth League title. |
| 2014 | Eden Hazard wins Chelsea F.C. Player of the Season for the first time. |
| 2014 | Chelsea Academy won the UEFA Youth League for the first time. |
| 2014 | Chelsea Academy began a historic run of five consecutive FA Youth Cup titles, marking a significant period of youth development success. |
| 2013 | Juan Mata wins Chelsea F.C. Player of the Season for the second time. |
| 2013 | Chelsea Under-21s (Development Squad) won the Premier League 2 championship for the first time. |
| 2012 | Juan Mata wins Chelsea F.C. Player of the Season. |
| April 20 2011 | Ryan Bertrand makes his Premier League debut for Chelsea at age 21 against Birmingham City. |
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This contents of the box above is based on material from the Wikipedia articles Chelsea F.C. Player of the Season & Chelsea F.C. Development Squad and Academy, which are released under the Creative Commons Attribution-ShareAlike 4.0 International License.