During his tenure, President Ong Teng Cheong locked horns with the PAP government over the sale of Post Office Savings Bank to the Development Bank of Singapore and his inability to obtain information about Singapore's reserves, which the government said would take 56 man-years to compile. Close to the end of his term, the Cabinet led by Prime Minister Goh Chok Tong said it would not support President Ong for another term, citing his poor health as the reason. Instead, they endorsed S. R. Nathan, who happened to be of Indian descent and this could keep the President's office rotated among different ethnic groups. President Ong himself also agreed, through a press conference, not to seek another term. Private tutor Ooi Boon Ewe applied for the Certificate of Eligibility but the Presidential Elections Committee ruled that he did not meet the necessary criteria. Also unsuccessful for a COE for a second time was Tan Soo Phuan, now DPP chairman. Nathan became the sole candidate granted the COE to file his nomination and won without a contest, prompting some critics to label the exercise as a "Presidential (s)election". Polling day, originally scheduled on 28 August 1999, did not take place.

Writ of election: 4 August 1999 [Wed]
Nomination day: 18 August 1999 [Wed]
President swearing-in: 1 September 1999 [Wed]

Electorate: 1,967,984

Election deposit: $30,000 (+$12,000)

Sellapan Rama NATHAN, 75

Ambassador-At-Large [M]