[2] In 1987, he joined the Singapore Legal Service as State Counsel and Deputy Public Prosecutor in the Attorney-General's Chambers (AGC).
During his tenure as a prosecutor, one of the cases prosecuted by Chan was that of Ng Theng Shuang, one of the two Malaysian armed robbers involved in the South Bridge Road shootout after their failed goldsmith robbery attempt.
[2] In August 1998, as Judicial Commissioner, Chan was the presiding judge of the trial of Too Yin Sheong, one of the three Malaysians accused of the brutal robbery-murder of Lee Kok Cheong, an associate professor of National University of Singapore, in December 1993.
[12][13][14] In April 2000, Chan heard the case of 33-year-old Vincent Lee Chuan Leong, one of the three kidnappers and mastermind of the abduction of a 14-year-old girl for ransom in September 1999.
[15] Subsequently, the other two kidnappers Shi Song Jing and Zhou Jian Guang, who were illegal immigrants from China, were also sentenced to life in prison by another judge Tay Yong Kwang during a separate trial.
[17] Chan was also the judge who sentenced Ipoh-born Malaysian Nagaenthran K. Dharmalingam to death after finding him guilty of drug trafficking.
[21][22] Chan was also the presiding judge during the trial of Azuar Ahamad, a logistics executive who was charged with sexually assaulting 22 women after befriending them and drugging them.