In an unprecedented move, Prime Minister Lee Hsien Loong went on national television to announce the dissolution of parliament and explained that the reason for holding an election while Singapore was battling Covid-19 was to secure a strong mandate to handle the economic challenges ahead. No GE had ever been held in that month as it was usually mid-term school holidays but this was replaced by school suspension during "Circuit-Breaker" in April and May 2020. The PAP government had also given out, in four budgets, close to $100 billion by dipping into the national coffers, including reserves, to save companies, jobs and help people tide over. The pandemic could turn worse nearer to the end of the parliamentary term and if polls could not be held by then, it would contravene the constitution.

To allay concerns of the public, the Elections Department introduced exceptional guidelines. Rallies and assembly centres were prohibited and traded with comprehensive TV broadcasts. No more than groups of five were permitted during campaign and the elderly who are more susceptible to Covid-19 would vote earlier. Wearing of masks and social distancing would also apply. For the first time, self-inking pens and counting machines would be used. The Covid-19 precautions at polling stations included voting for those unwell from 7 pm to 8 pm, although voting was extended to 10 pm due to delay caused by additional checking measures.

The Electoral Boundaries Review Committee report, which was released on 13 March 2020, canned six-member GRCs for the first time since 1997, although they were still provided for under the Singapore Constitition. The four-month lead time did not give advantage to the opposition as outreach activities had to be halted under "Circuit-Breaker" restrictions. Election deposit was reduced for the second consecutive GE to the same amount as in the 2006 and 2016 polls. A vacant seat in Marsiling-Yew Tee GRC was due to Halimah Yacob's ascension as President of Singapore in 2017.

This was the last election PM Lee would lead the PAP into before handing over the reins to his successor, Deputy PM Heng Swee Keat, who is likely to become Singapore's fourth PM. Despite suffering a stroke in 2016, Heng was the choice of the younger generation of ministers. He invited rumoured "fellow PM front-runner" Chan Chun Sing to be his deputy should he ascend to the top post and the latter agreed. The PAP's slogan would be "Our Lives, Our Jobs, Our Future". Veteran politician and former PM Goh Chok Tong retired as Member of Parliament in this election.

Another veteran, Low Thia Khiang, who made way for Pritam Singh to become leader of the sole parliamentary opposition WP two years ago, would also retire along with fellow Aljunied GRC MP Chen Show Mao. Chen first appeared as a "star candidate" in 2011, while the "star candidate" of NSP in the same election, Nicole Seah, stood under WP this time. In a rare occurence in Singapore politics, Chen mounted a leadership challenge against Low in 2016 but the party remained united. Meanwhile, Pritam, Low and WP chairman Sylvia Lim had lost a civil suit involving overpaying the managing agent of their town council and their appeal against the verdict was pending. WP would be campaigning on "Make Your Vote Count" to prevent a wipeout of opposition in Parliament, a tactic PAP rebutted by showcasing the Non-Constituency MP scheme.

Sights on the opposition were also on the new PSP set up by Dr Tan Cheng Bock. The presidential candidate in 2011 became one of the rare former PAP MPs to venture into opposition politics, the second to do so after Low Yong Nguan who joined SDP in the eighties. Campaigning on the slogan "You Deserve Better", PSP was endorsed by Lee Hsien Yang, younger son of the late Lee Kuan Yew and brother of PM Lee whom he and their sister Lee Wei Ling had fallen out with over the demolishing of their late father's house as stipulated in a will. His wife had been found guilty of misconduct over the execution of the will, while their son faced contempt of court charges. Both Lee siblings charged that the cases were politically-motivated. Dr Tan was the oldest candidate in the polls and the youngest, Choo Shaun Ming, was also from his party.

Apart from PSP, two other new opposition outfits were established after the 2015 election. One was PV by former NSP leader Lim Tean. Another was RDU, spearheaded mostly by brief PSP members and registered just before the polls. The short runway did not hinder it from producing a manifesto entitled "Explore New Directions Together" but it fared badly as it went against popular PAP figure, former DPM Tharman Shanmugaratnam. Opposition parties that contested the last GE were largely demoralised and inactive after their drubbing, with most of them fielding a smaller slate this time. Still, the crowded field of 11 participating parties, the most since 1959, led to the first GE three-corner GRC fight between PAP, PV and SDA, whose component PKMS was putting up more than one candidate for the first time since 1991.

In SPP, former NCMP Lina Loh followed her husband Chiam See Tong's footsteps to retire from politics and gave way to a new leadership that included former NSP leader and another NCMP Steve Chia. Their slogan would be "A Better Tomorrow". SDP chief Dr Chee Soon Juan returned to the seat he contested in the by-election of 2016 and his party slogan was "4 Yes 1 No". However, one "No" to pushing for a "ten million population" was denounced by PAP as falsehood as the government had no intention to do so.

Attempts by RP, PPP, DPP and SingFirst to register their own alliance or join SDA did not come to fruition. With the slogan "Build Back Better, Fairer", RP's only GRC team consisting of Kenneth Jeyaretnam went to Ang Mo Kio GRC helmed by PM Lee, making it a contest between the sons of the late Lee and opposition legend J. B. Jeyaretnam, both whom often crossed swords during their political careers when they were alive. PPP was as good as putting out an independent, the first time since AI in 1988 that a party fielded a solo candidate. DPP sat out, while Tan Jee Say dissolved SingFirst that he led to rejoin SDP.

Despite an uncertain future ahead in the thick of Covid-19, memories of high-profile lapses and declining quality of public services since 2015 lingered, such as cyber-security breaches, miltary training deaths, governance of personal mobility devices and postal efficiency. On top of these, the pandemic spread within cramped worker dormitories, amendments to the last presidential election rules, introduction of an anti-fake news law and controversy surrounding a PAP candidate, Ivan Lim, did not sit well with some. People who knew Lim went public to say that he would be an unsuitable MP due to displays of bad behaviour and he opted to drop out. As such, the long-drawn call for checks and balances in Parliament appeared more effective than the past. Apart from this, the "internet election" evened the playing field. Incidentally, ethnic minorities were contesting six or nearly half of the single wards and make up four out of five of PSP's Nee Soon GRC team.

Although DPM Heng shifted to East Coast GRC to stymie a possible WP win there, Sengkang GRC, which encompassed the former Punggol East single ward once held by WP, became the second group constituency to fall to the opposition. One of the elected candidates, Raeesah Khan, had her past Twitter posts that were deemed racist and possibly in contempt of the judiciary flagged out. Daughter of Farid Khan, a disqualified aspirant in the 2017 Presidential Election, she apologised for them while police investigations commenced. This did not dampen her team's chances and she displaced her precedessors Ho Kah Leong in 1966 and Tin Pei Ling in 2011 as the youngest MP since independence. Overall, WP won a majority vote in its contested wards, another first for a non-PAP party.

RP had given way to PSP in West Coast GRC as it encompassed the Ayer Rajah ward, which Dr Tan once represented for decades. Although none from PSP won, the maximum number of NCMP seats for defeated opposition candidates had been increased from nine to 12 and Dr Tan's GRC team was eligible for two after WP bagged ten seats. PSP took them up, sans Dr Tan who felt he had been in Parliament for many years before and there was no need to return just to voice out.

Nonetheless, with its victory, PAP would set an international record among countries with universal suffrage before the end of the parliamentary term in 2025. Not only would it be the second-longest governing party with 66 years of unbroken rule after Mexico's Institutional Revolutionary Party that governed the North American country for 71 years from 1929 to 2000, it would have overtaken Malaysia's National Front and its preceding Alliance Party that lost power in 2018 after 64 years. Not only did the pandemic not hamper voter turnout, rejected votes fell to the lowest level nationwide and in a particular constituency, Punggol West, since 1963. PM Lee decided to appoint Pritam as Official Opposition Leader to recognise the desire of voters for an increased opposition presence.