Breaking tradition from past Presidential Elections, the last two being uncontested, this turned out to be a tight multi-corner race with four candidates receiving the Certificate of Eligibility from the Presidential Elections Committee. Three were once members of the ruling PAP, each serving at the different levels of ministerial, backbencher and grassroots, while the last stood as a SDP candidate in the General Election four months earlier. The coincidence of all four bearing the surname "Tan" was a subject of amusement in the social media.

Former Deputy Prime Minister Tony Tan, who resigned as chairman of Singapore Press Holdings and from the Government Investment Corporation to contest, was backed by the outgoing President, several PAP ministers, associations and unions. Campaigning on the slogan "Confidence for the Future", he was perceived to be the PAP government's endorsed candidate despite flashing independent credentials and evetually won to become Singapore's seventh President. His strongest opponent turned out to be ex-PAP Member of Parliament Tan Cheng Bock, most remembered for his resounding victories in the Ayer Rajah ward and being a vocal internal critic. He did not back down despite Tony Tan's entry and his slogan was "Think Singaporeans First".

The two, who were fellow PAP Parliamentary colleagues for seven terms, had much in common. Both were born in the same year, entered politics one year apart (in 1979 and 1980), stepped down as MPs in 2006 and resigned from PAP just before this election to fulfill the compulsory criteria of non-partisanship. The nail-biting finish between the two triggered a nationwide recount and set a record for the second narrowest margin after the 1959 River Valley contest.

The third, Tan Jee Say, was the former principal private secretary to then-DPM Goh Chok Tong. As the only former opposition candidate, being granted a COE was unexpected for many observers, as his credentials were also thought to be insufficient to meet the criteria. He campaigned on "Heart of the Nation" and his symbol of a heart was also used by the late Ong Teng Cheong, Singapore's first Elected President.

The fourth and only newcomer, Tan Kin Lian, was formerly chief executive officer of NTUC Income, the trade union movement's insurance cooperative, and secretary of PAP's Marine Parade branch helmed by Goh, now Emeritus Senior Minister. After stepping down as CEO, he resigned from PAP and became critical of the government, especially over the Lehman Brothers mini-bonds saga. His slogan was "Voice of the People".

A total of six applications were submitted. Two others who failed to qualify for the COE were Andrew Kuan and Ooi Boon Ewe, attempting their second and third application respectively, with the latter resigning from the PLDP he founded.

This was also the first time since independence that two national elections were held in the same year, photos of candidates were included in ballot papers to prevent confusion and a Presidential candidate's deposit was forfeited. A mild delay in the transportation of overseas votes was caused by a hurricane disaster in the United States and temporary airport closures in New York.