Yeon Woo-jin began his entertainment career as a model before making his acting debut in the short film Just Friends? in 2009. In 2012, he led the four-episode KBS2 series Just an Ordinary Love Story, which won him Best Actor in a One-Act/Short Drama at the KBS Drama Awards. That same year, he acted alongside Lee Jun-ki and Shin Mina in the fantasy sageuk Arang and the Magistrate, in which he was nominated for Best New Actor at the MBC Drama Awards. In 2013, he appeared in the MBC romantic melodrama When a Man Loves, in which he bagged an Excellence Award nomination at the 6th Korea Drama Awards. In 2015, he was nominated for another Excellence Award at the SBS Drama Awards for the romantic comedy Divorce Lawyer in Love. In 2017, he headlined the SBS legal drama Nothing to Lose, which earned him a Top Excellence Award nomination at the SBS Drama Awards. In 2019, he was paired with Kim Se-jung in the KBS2 series Let Me Hear Your Song, which scored them a nomination for Best Couple at the KBS Drama Awards.

Yeon Woo-jin completed his mandatory military service before he debuted in the entertainment industry.