The two GEs under his purview thus far, 2006 and 2011, unfolded like clockwork over near-identical time frames, from the release of new electoral boundaries at the end of February, to the dissolution of Parliament in the third week of April, to Polling Day on the first Saturday of May.
By this schedule, the GE should be held only in May 2016.
But this time around, will PM Lee abandon regularity in favour of political momentum?
Logic would suggest that the date of a GE should, by simple political calculation, coincide as much as possible with periods of support for the ruling party, of which the Prime Minister is secretary-general. And earlier this month, at the annual May Day Rally - traditionally an opportunity to emphasise the Government's agenda on workers and wages - Mr Lee delivered an unexpectedly electoral speech, declaring that the most important issue in the next GE would be leadership renewal.
Noting that Singapore's success hinges on it being led by exceptional leaders, he pointed to the strong reaction of Singaporeans to the death of founding prime minister Lee Kuan Yew in March. They were reminded that it was exceptional leadership which brought the nation to where it is today, said PM Lee.
Indeed, Mr Lee's death and the strong reaction to it is a key factor in many observers' belief that a GE is now imminent.
"Elections this year would allow the Government to capitalise on the inextricable link between founder Lee Kuan Yew and the People's Action Party," said a report by research firm BMI last week.
Another research firm, Blackbox, said that its monthly survey of 1,000 Singaporeans aged 15 and above threw up a link between the death of Mr Lee and a 20 per cent drop in the number of Singaporeans "who think that the PAP's vote in the next GE will be lower than in 2011".
The ground seems sweet for the ruling party right now, Blackbox added, noting that its survey over the last year showed "steady improvement in community satisfaction" on hot-button issues like foreign worker inflows.
But would an early GE in 2015, coming after Mr Lee's death and coinciding with jubilee celebrations, play well with today's voters? Insight examines three window periods when Singaporeans might head to the polling station.
THREE of the past 11 elections - in 1972, 1988 and 1991 - were held in August and September. The common denominator spurring their timing, of course, was the rousing, traditional appeal to nationhood, the end-August National Day Rally speech.
This year, the Prime Minister's annual address to the nation is likely to be on Aug 23.
So, if the electoral levers are thrown into motion immediately after this year's rally, Singaporeans could be heading to the polls as soon as early September. Observers favour the September/October option simply because it is the nearest available window in sight to hold a GE.
The next few months are occupied with the SEA Games and then the jubilee National Day Parade. This makes a post-National Day Rally GE the earliest possible opportunity to leverage on the success of those events, and on the goodwill generated by policies introduced over the past few years, from MediShield Life to the Pioneer Generation Package, to measures to control housing prices and the inflow of foreign workers.
"Most of the ground issues have been addressed, so my sense is that the earlier the GE is, the better, because you can't tell what will happen next," says PAP MP Zaqy Mohamad (Chua Chu Kang GRC).
"September or October is logical because of the feel-good factor with the SEA Games and the SG50 celebrations," he adds.
The death of founding prime minister Lee Kuan Yew in March will have a galvanising effect, says PAP MP Inderjit Singh (Ang Mo Kio GRC).
"Mr Lee's passing and the mourning period was an opportunity for all Singaporeans to gain a better perspective of the journey our leaders had taken to give us a comfortable Singapore," he says.
"Some took (Singapore's success) for granted, but Mr Lee's passing has helped galvanise the nation."
But several observers note the possibility that Singaporeans might be event-weary by then. Some voters might even be put off by a perceived attempt to extract electoral mileage from both the low of mourning and the high of jubilee-year celebrations.
"Let the people rest after all the hullaballoo," says political observer and opposition veteran Wong Wee Nam, referring to SG50 celebrations. "A high can cut both ways."
The short timeline would also fuel charges that the Opposition was not being given enough time to prepare for elections. The Workers' Party (WP) is in the midst of court proceedings brought by the Ministry of National Development in which the former is trying to prevent independent accountants from being installed in the Aljunied-Hougang-Punggol East Town Council.
It is also scrambling to make a June 30 deadline for the submission of an audited set of FY2013 accounts.
These WP activities come after the Auditor-General's findings of severe lapses in compliance and governance at the only Opposition-run town council in Singapore.
The Singapore Democratic Party seems the most prepared for GE; it launched its election slogan and GE plan in January.
But the rest of the Opposition scene is in flux. The National Solidarity Party (NSP) saw a leadership shake-up recently that had key members resign, while new parties like SingFirst - headed by former presidential candidate Tan Jee Say - and People's Power Party - headed by former NSP secretary-general Goh Meng Seng - have just sprung up.
2. Festive year-end
A GENERAL Election in the Christmas festive season used to be a favourite of founding prime minister Lee Kuan Yew.
He called three consecutive year-end GEs in 1976, 1980 and 1984. And in 1997, then Prime Minister Goh Chok Tong called a GE that saw Singaporeans spend Christmas Day at election rallies and Jan 2 at the polling station.
The political assumption was that people were in a good mood during this time of the year, flush with yuletide cheer, not to mention cash from yuletide bonuses.
Observers view a year-end GE as providing a sufficient separation in time from the climax of SG50 celebrations, with over four months between the National Day Parade and the end of the year for political parties to make their cases, and candidates to walk the ground.
Singapore Management University law don Eugene Tan favours the year-end as this would "give some distance and allow voters to be more reflective". "The stress levels among Singaporeans are lower during year-end, which puts them in a good position to deal with weighty issues the GE might throw up," he adds.
Notes PAP MP Zaqy Mohamad (Chua Chu Kang GRC): "It would be seen as having a balance, giving the Opposition time to make preparations."
Adding to the positive vibe, MediShield Life, which will cover every Singaporean regardless of age, is also likely to come into effect by year-end.
On the other hand, with many Singaporeans travelling over the school holidays, voter turnout at such a GE would be low, and polling day would also have to avoid the Deepavali celebrations, including the Nov 10 public holiday.
School examinations rule out the early November window, while Prime Minister Lee Hsien Loong's schedule rules out the second half of November.
PM's busy schedule will see him travel to back-to-back international summits, starting with the Group of 20 meeting in Turkey on Nov 15.
Then, there is the Asia-Pacific Economic Cooperation meeting in the Philippines on Nov 18, the Asean Summit in Kuala Lumpur directly afterwards, and the biennial Commonwealth Heads of Government Meeting slated for Nov 27 in Malta.
This schedule would mean that a domestic campaign can start in earnest only after his return, leading to a January polling date - dangerously close to when a new Budget must be presented by the Government and passed by Parliament to keep the state running.
3. In May next year
THE feverish speculation seemed, in hindsight, wholly unnecessary.
After months of guessing games, the 2011 General Election ultimately took place on a schedule that matched, to the day, that of the GE that came before it in 2006.
Some put it down to a mathematician's inclination towards regularity - Prime Minister Lee Hsien Loong, with whom the ultimate decision on election timing rests, has a first-class honours degree in maths from Cambridge.
Others saw it as fulfilling the wishes of a new generation of voters for a fairer electoral landscape, in giving time for the Opposition to swing into gear.
"Keeping it to a five-year cycle reduces the accusations that this gives the ruling party an advantage," notes Singapore Management University law don Eugene Tan.
It is for this reason that some observers hope to see PM Lee stick to the same time frame for the third GE running and call polling day on the first Saturday of May next year - despite the fact that the May 2011 GE saw the People's Action Party's worst performance at the polls.
"Sticking to a May 2016 GE would also mean one last Budget for the Government to give away all the good things," notes opposition veteran and political observer Wong Wee Nam, referring to the cash handouts that have defined election-year Budgets in the past.
The Government's coffers still have an unspent $4 billion in surplus after this year's Budget.
Avoiding the jubilee year would also allow the PAP to sidestep charges of capitalising on national sentiment, while allowing the spotlight to stay on key crescendo SG50 events scheduled for end-2015 - like the opening of the much-awaited National Gallery.
Having the GE in the Chinese zodiac Year of the Monkey would also invoke an auspicious precursor: The last time a GE was held in the Year of the Monkey - 1980 - was also the last time the PAP managed to win every seat in Parliament.
But waiting another year before holding the GE would expose the ruling party to the possibility of a black swan event or a slowing economy.
For example, economists expect the United States Federal Reserve to hike interest rates at the end of the year. This could cause a drag on the Singapore economy in the months leading up to when an election might be called.
But OCBC economist Selena Ling says economic factors are not an electoral game-changer as the growth outlook looks to be steady at 2 to 4 per cent a year.
"The most ideal time for GE is when you have something to show, whether in terms of growth or increased labour productivity," she adds. "We are half way through the economic restructuring story, and we haven't reaped the fruits yet."
Then there are those who believe that the PAP has been too kind - and too fair - for its own good.
The five-year cycle was blamed by some as a factor in its 2011 showing - 60.1 per cent of the vote share, a historic low, and the loss of Aljunied GRC to the Workers' Party.
The schedule gave the Opposition too much lead time to stir up sentiment against the PAP, many of the party's own rank-and-file believe.
So it is perhaps no surprise that party stalwarts do not want to wait another year before meeting voters.
"I don't think it is wise to wait too long," says veteran MP Inderjit Singh. "I believe that PM has already identified the (ministerial-calibre) people he needs (to bring into politics), and many policies have already been changed, or announced, that will improve the lives of Singaporeans.
"So, from all angles, there is little value in waiting."