In 2007 and 2008, Chen went on to direct Ah Ma and Haze respectively. Both attracted favourable criticism. Ah Ma was awarded a Special Mention in the short film competition at the prestigious Cannes Film Festival, making it the first Singaporean film to win an award at the festival.

In 2009, Chen married Rachel Yan, whom he met while staying in London in 2007. Their son was born in August 2018.

Following his mandatory conscription in the army, Chen was admitted to the National Film and Television School (NFTS) in the United Kingdom. Graduating in 2010, two of his short films, Distance and Lighthouse, were released that year. These were followed up with Karang Guni (2012) and Homesick (2013).

Ilo Ilo, Chen’s first feature film, was released on August 29, 2013 in Singaporean theatres. Chen served as director, producer, and writer. According to Chen, the film was inspired by a real life maid who worked for Chen’s family when he was a child. After its world debut at the 2013 Cannes Film Festival, Ilo Ilo received a fifteen-minute long “standing ovation” and earned Chen the coveted Camera d’Or. Prime Minister of Singapore Lee Hsien Loong noted Chen’s achievement, congratulating him and the film’s cast on Facebook.

On 19 October 2013, Ilo Ilo went on to win the Sutherland Trophy for the Best First Film at the London Film Festival. (The same night, one of Chen’s tutors at NFTS, Pawel Pawlikowski, won the Best Film Award for Ida).

In September 2015, it was announced that Distance, an “omnibus film” for which Chen served as executive producer and writer, will open the 2015 Golden Horse Film Festival in Taiwan. Distance consists of segments by the three directors Xin Yukun, Tan Shijie and Sivaroj Kongsakul, from China, Singapore and Thailand respectively.

In spring 2018, Chen began production on his second feature film, Wet Season, which reunites him with Ilo Ilo stars Yeo Yann Yann and Koh Jia Ler.