By election was held on 29 June 1957 while the nomination day occurred on 18 May 1957 in Cairnhill and Tanjong Pagar was due to David Marshall from Labor Front's resignation as Chief Minister on 7 June 1956 after his initiated talks with British authorities for self-governance broke down. He had also challenged opposition leader Lee Kuan Yew from the People's Action Party to resign and recontest their respective constituencies as well which Lee did accept and follow the move, but to see David Marshall's retirement of politics on a fear of speculations of bloodly street protests and lost the seat to a new party Liberal Socialist Party while Lee Kuan Yew had retained his seat in Tanjong Pagar.