Between 1963 and 1981, Anson was largely uncontested with small minority parties contesting it time to time.
In 1981, incumbent MP and NTUC Unionist, Devan Nair resigned from the PAP and the Parliament to accept the then largely ceremonial office of President as the country's head of state. This resulted in the third time Anson had a by-election. Nominations for the by-election started on 21 October. Three candidates were nominated for the by-election: PAP had Pang Kim Hin, the nephew of former minister Lim Kim San; Workers' Party (WP) secretary-general J. B. Jeyaretnam; and United People's Front Harbans Singh. Chiam See Tong, who recently founded Singapore Democratic Party (SDP) a year prior to the by-election, expressed interest but withdrew later and backed Jeyaretnam.
The by-election was eventually won by Jeyaretnam of WP, breaking PAP's monopoly of full dominance in Parliament, the first time in Singapore since 1968 an opposition party had won a parliamentary seat. Between 1981 and 1984, Jeyaretnam was the only opposition MP in Parliament. He will go on to be MP for Anson and also win with increased votes in the 1984 Singaporean general election along with SDP's Chiam See Tong in Potong Pasir Constituency.
On 10 November 1986, Jeyaretnam lost his parliamentary seat following his convictions for making false statements. No By-Elections were called for the vacated seat for 2 years and no one represented Anson between 1986 and 1988.
In 1988, the constituency was dissolved following the establishment of GRCs and SMCs.
Note: The Elections Department does not include rejected votes when calculating the vote shares of candidates. Hence, all candidates' vote shares will total to 100% at any given election (may not appear so in multi-way contests due to rounding).