He is best known for his leading roles in Bread, Love and Dreams (2010), My Cute Guys (2013), Hit the Top (2017), Grand Prince (2018) and Your Honor (2018), Nokdu Flower (2019), Psychopath Diary (2019–2020), and Train (2020).

[citation needed] Yoon debuted in the daily sitcom High Kick Through the Roof and rose to fame for his role as a semi-rebellious teenager.

[5][6][7][8] Due to the drama's popularity, Yoon and co-star Lee Young-ah were named promotional ambassadors for North Chungcheong Province.

[9] The same year, Yoon had his first big screen debut with a leading role in the horror movie Death Bell 2: Bloody Camp.

[12] In 2011, Yoon was cast to replace Kim Jaewon, who withdrew after suffering from multiple injuries on the first day of filming, in the romantic-comedy Me Too, Flower!.

He played a millionaire masquerading as a parking attendant and entering into relationship with an abrasive female police officer (Lee Ji-ah).

In 2012, Yoon starred in the Japanese web drama Brand Guardians, based on a story about a Korean youth who travels to Japan to make it as a fashion stylist.

[20] In October, Yoon was cast in KBS's romantic comedy series Prime Minister & I alongside Lee Beom-soo and Girls' Generation's Yoona.

[22] After completing military service, Yoon starred in JTBC's historical fantasy drama Secret Healer, playing Joseon's famous doctor Heo Jun.

The drama is a fictional story about a young Heo Jun and his journey to lift a curse for a princess (played by Kim Sae-ron), whom he later fell in love with.

Yoon plays a naive and pushover stockbroker, who begins to believe he is a psychopathic murderer after an accident which results in amnesia and the discovery of a diary in his possession.