In 2009, actor Yoon Si-yoon made his official debut by playing the role of Junhyuk student in "High Kick Through the Roof". At that time, thanks to this drama, she and Shin Se Kyung won the Best On-Screen Couple Award at the 2009 MBC Entertainment Awards.
In 2010, Yoon Shi-yoon starred in the KBS TV series "Bread King Kim Tak-gu" (except for the author and director, everyone else in the crew opposed her taking this role). The finale of the series ended with a ratings of 50.8% ( TNMS National Ratings Benchmark) ended, setting a record for the highest ratings since it was broadcast on 3 David TV in 2010. Yoon Shi-yoon won the "2010 Korean TV Festival Male Newcomer Award" and "2010 KBS Drama Awards for Outstanding Feature Drama" for his role as "Kim Tak-gu" Actor Award" and many other awards. In July of the same year, Yoon Shi-yun's first movie "Dead Exam 2: Teaching Internship" was released. On July 20th and September 5th, he participated in the recording of "Strong Heart" and "Night Planet - Bread King Kim Tak-gu Special" respectively. On November 16, he participated in the awards ceremony of the 31st Blue Dragon Film Festival in South Korea.
On January 20, 2011, Yoon Shi-yoon attended the "20th HIGH1 Seoul Music Awards" as an award presenter. In September, Yoon Shi-yoon guest-starred in another sitcom "High Kick 3" directed by director Kim Byung-wook, playing the role of Park Ha-sun's first love in the memories. In the same month, the "Singles Barefoot Youth Magazine Pictorial" was shot. In October, she took over the filming of the MBC TV drama "I am a flower too". In the drama, Yoon Si-yoon plays the role of Seo Jae-hee who hides her identity as the CEO of a women's handbag company and works in a parking lot. Her different costumes suitable for the two identities add color to the drama. . As a CEO, he wears a gentleman's luxurious look, but as a parking lot worker, he transforms into an approachable and slightly comical image, showing a completely different and opposite charm. On December 30, Yoon Shi Yoon held a signing event at the OMPHALOS store on the second floor of HomePlus in Bucheon, Seoul.
In 2012, the Sino-Korean cooperative TV series "Happy Noodles" starring Yoon Shi-yoon was officially launched in Hangzhou, China in May. On November 30 of the same year, Yoon Shiyun participated in the "2012MAMA" awards ceremony held in Hong Kong and appeared on the MAMA stage as a guest.
In January 2013, Yoon Shi-yoon chose the humorous tvN TV series "Flower Boy Next Door". In the drama, Yoon Shi-yoon appeared as the sunny little hazelnut Enrique Kim, playing a modern person happily and joyfully. voyeuristic psychology. Taking off Kim Tak-gu's sincerity and the heavy coat of the long drama, he returned as a sesame candy. His heart-wrenching yet sunny appearance once again captured the attention of women in 2013, and he became a completely charming man. Although Xiao Hazel's fans once again pushed him to the position of a powerful actor, he always followed his own path step by step. On February 23, Yoon Shi-yoon attended the "1st Asia Style Festival" co-organized by bntWorld and the All-Korean Scholars and Scholars Association. On March 23, Yoon Shi-yoon appeared as a special guest as a friend at the concert held by Korean male singer Lee Jung in Seoul. She wore a sky blue outfit to perform and stole the spotlight. On April 21st, he co-hosted the SBS variety show "Barefoot Friends" with members such as Kang Ho-dong and Yoon Jong-shin for the first time. Yoon Shi-yoon, a newcomer in the entertainment industry who was called a "rising variety star" by the Korean media, showed his sincerity and kindness , her down-to-earth personality and cute makeup-free image are active in a new variety show for the first time. On April 28, "Happy Noodles", filmed in China, was launched on Zhejiang Satellite TV, and its ratings continued to rise. In the fierce competition among prime-time hit dramas, it has repeatedly topped the ratings list. In the drama, Kang Soo-chan, played by Yoon Shi-yoon, moved many viewers with her invention of happy noodles. Compared with the previously filmed "Bread King Kim Tak-gu", although the two dramas have the same theme, they are still different in various aspects. The TV series "Happy Noodles" takes the story of noodles as the main line and uses food to explain love and the true meaning of life. In comparison, one is Western-style noodles and the other is Chinese cuisine, and the styles are very different. On April 20, Yin Shiyun attended the Beijing press conference together with Li Feier, Zhang Junning, Gao Shuguang and other main creators. On the same day, after learning of the sudden earthquake in Ya'an, Sichuan, the press conference temporarily added a blessing segment. All the main creators wrote blessings on the spot to cheer for Ya'an and convey the positive energy of "happiness". On September 1st, Yoon Shi Yoon went to Japan to promote "Flower Boy Next Door", and with the enthusiastic response from fans, an additional performance was successfully held in a fiery atmosphere, confirming its high popularity in Japan.
In December of the same year, he took over the filming of the KBS 2TV new moon drama "The Prime Minister and Me", in which he played the role of Kang In-ho, the accompanying section chief who determines the presidential power and laws. With his neat short hair and the fact that he lost 7kg for the TV series, he has a more cheerful and cheerful appearance. He plays Kang In-ho who is sometimes ruthless and sometimes gentle. In the drama, we see a look that is completely different from Yoon Shi-yoon. Of course, different acting transformations are greeted with applause from the audience. On December 5, Yoon Shi Yoon and the crew participated in the recording of the variety show "Happy Together". On the 27th, Yoon Shi Yoon, Lee Hwi Jae and Miss A member Bae Suzy served as the host of South Korea's "2013 KBS Music Festival".
On January 16, 2014, Yin Shiyun was invited by Chengtian Jiahe Entertainment Co., Ltd. to Hong Kong to serve as the opening guest of "the sky". On the evening of March 27, Yoon Shi Yoon attended the Baek Expert VIP trial writing session. On April 3, the movie "Baek Expert" starring Yoon Shi-yoon was released in theaters across Korea. The famous professional golfer Baek Se-jin, played by Yoon Shi-yoon, lost everything due to a drunk driving accident, so he ended up on a small island with only six students. A school that is about to be abolished, and the story of struggling and growing up with the school's boss Lee Byung-joo (played by Yeo Jin-goo). On April 28, Yoon Shi-yoon quietly enlisted in the Marine Corps Education and Training Corps in Pohang, North Gyeongsang Province. After seven weeks of basic military training, he will be assigned to the Marine Corps to begin his nearly two-year military life.
On January 27, 2016, Yoon Shi-yoon ended his military service and officially retired from the Second Marine Division of Incheon. On March 8, Yoon Si Yoon was confirmed to star in JTBC's new drama "The Witch's Guide", playing the male lead Heo Jun. The play tells the love and growth story between Princess Ruili, who turned into a white-haired witch due to a curse, and Xu Jun, a passionate youth. This drama is Yoon Shi Yoon's return after being discharged from the army, and it is also his first challenge to a historical drama, so it is highly anticipated by fans. In addition, the drama will take over from "Asahi Clan's Southern Conquest" and will be broadcast in May.