In his first electoral outing as party chief, Workers' Party (WP) secretary-general Pritam Singh seemed to have taken a conservative approach.
The party seemed content to defend its home turf of Hougang SMC and Aljunied GRC, as it fielded fewer candidates and contested just six constituencies, compared with 10 in 2015.
It was to have been a night of no alarms and no surprises.
But instead, the WP grabbed Sengkang GRC from the People's Action Party (PAP) with 52.13 per cent of the votes. In the process, it took down Minister in the Prime Minister's Office and labour chief Ng Chee Meng and office-holders Lam Pin Min and Amrin Amin with a team made up of only one experienced candidate and three new faces.
The opposition party also retained Hougang and Aljunied with comfortable margins, improving on their 2015 showing.
The results would likely have exceeded the party's own expectations given the uncertainties at the start.
Three of the party's six incumbent MPs, including WP icon Low Thia Khiang, did not contest the 2020 polls.
It was also thrown a curve ball on Nomination Day when Deputy Prime Minister Heng Swee Keat was moved from Tampines GRC to defend East Coast GRC for the PAP.
This move appeared to have closed off the party's chances for winning another GRC in the near term. It had been slowly making inroads in East Coast since 2006, but would now have to look elsewhere.
Perhaps already pre-empting this, since it was widely expected that the ruling party would send a heavyweight to defend East Coast, the WP did not field its next best team there. Instead, it sent its next best candidates to different constituencies, with lawyer He Ting Ru, a popular candidate in the 2015 General Election, sent to the new Sengkang GRC.
Along with economist Jamus Lim, equity analyst Louis Chua and social activist Raeesah Khan - the party's most talked about new faces - this became widely considered as the WP's B team.
The strategy appears to have paid off, with all of the WP's teams turning in better results this time round compared with 2015.
The party was stopped in East Coast GRC, but not quite in the way most had expected, with its team garnering 46.59 per cent of the votes.
In Marine Parade, the WP received 42.24 per cent of the votes, and even in the new Punggol West SMC, it received 39.03 per cent.
But it was in Sengkang that the party pulled off the biggest upset.
Fielding Dr Lim in the constituency turned out to be a masterstroke.
Even before the election, his qualifications had created a buzz online. After plaudits poured in for his performance in a televised debate, the quartet's popularity and profile grew.
The constituency's population also played to the party's advantage. More than 60 per cent of Sengkang GRC residents are aged below 45, larger than the national average.
That the WP candidates in Sengkang ranged in ages from 26 to 44 also made it easier for young voters to identify with them.
It seemed the team could do no wrong. Even after it was revealed that police reports had been made against Ms Raeesah, in relation to social media comments she had made in the past alleging discrimination by Singapore's law enforcement authorities, the party managed to avert an all-out crisis. It immediately called a press conference where Ms Raeesah, head bowed, apologised for her "insensitive" and "improper" remarks.
As it turned out, the episode might have gained the team more support.
While the Sengkang win was a surprise, the party's overall showing indicates it was no fluke.
When the party lost Punggol East SMC and barely retained Aljunied GRC in 2015, many took it as a sign that there was nothing inevitable about the drift towards the opposition as Singapore matures.
But in the face of this morning's results, it is perhaps time to reassess this perspective.
That the WP was able to achieve such a vote share, amid a pandemic which typically sends voters into the arms of the PAP in a flight to safety, is the best indication that it may have finally gone beyond its hardcore of supporters to win over some of those in the middle.
And if it was not clear before whether voters had bought into its argument of constructive politics, its showing this time perhaps confirms that it has pitched its message just right.
While stressing that it would not needle or needlessly obstruct the PAP in Parliament, it sought to convince voters that a diversity of voices was what Singapore needed.
Amid a mood kept subdued by the pandemic, the party also took the chance to burnish its moderate image - successfully walking the line between a call for change and not rocking the sampan that is Singapore.
If Mr Singh can capitalise on the momentum gained from the polls to build up the WP, he may take his party much further than his predecessors.