Jackichand Singh began his professional career at Royal Wahingdoh in 2009 and helped the club gain promotion to Hero I-League for the 2014-15 season. FC Pune City bagged the winger for the 2015 Hero ISL edition, where he scored one of the fastest goals that season. His speed and guile on the wings make him a potent threat against any opponent. In Hero ISL 2017-18, he made 17 appearances for Kerala Blasters and scored two goals and provided three assists. This will be his second stint in the state of Goa, after having played for Salgaocar FC in Hero I-League 2015-16.