Those arrests marked a turnaround from 2014, when the trio helped bring out hundreds of thousands of people to the streets to call for a more direct form of democracy in the former British colony.
While Sunday's march sought to echo the optimistic spirit of those protests, some expressed concern about a lack of direction in the opposition camp amid ongoing government prosecutions and tightening restrictions on political expression.
"When you're facing an authoritarian regime, the best they can hope for is for people to stay silent," said Avery Ng, a protest leader and chairman of the League of Social Democrats.
In addition to Wong, Law and Chow, multiple other Umbrella activists are facing prosecution, including Benny Tai, a Hong Kong University professor who first suggested the 2014 protests.
"Never in Hong Kong's history have so many opposition politicians and activists faced court proceedings against them," according to Kong Tsung-gan, author of "Umbrella: A Political Tale from Hong Kong."
Kong has documented 39 cases
against 26 pro-democracy leaders and activists since the protests, of which 21 are still ongoing.
The Hong Kong government has consistently denied accusations that cases have been brought for political purposes.
Sunday's march singled-out Justice Secretary Rimsky Yuen, seen as the driving force behind many of the prosecutions. Speaking to CNN last week
, Chris Patten, the last British colonial governor of Hong Kong, criticized Yuen for pursuing jail terms for Wong and others after their case appeared settled.
"He didn't have to ask for a review of the original (community service) sentences," Patten said, adding that doing so risked undermining Hong Kong's reputation as "an international hub for the rule of law."
Writing from prison this week
, Wong said "being locked up is an inevitable part of our long, exhausting path to democracy."
His and other jailed protesters' faces were a frequent sight on banners and leaflets at Sunday's march. Protester Danny Chan said older Hong Kongers like him "need to speak out, to support the young people in jail."
Limits on speech
Many in the opposition camp fear growing restrictions on speech and political activity, with the shadow of a forthcoming anti-sedition law
This week lawmaker Cheng Chung-tai was found guilty of "desecrating" the standards of China and Hong Kong and fined $640 after he flipped over some plastic flags brought into the city's parliament by pro-Beijing legislators during a session last year.
A law recently passed by China's National People's Congress will also criminalize insulting the country's anthem, "March of the Volunteers."
While it is unclear how the law will apply in practice to the city, which has greater freedom of speech protections than China, the national anthem has been a key point of protest in Hong Kong, with local soccer fans repeatedly booing it during matches with China.
"Using laws to mandate 'patriotism' curbs the freedom of expression and reflects an increased degree of authoritarianism in Hong Kong," said Jeffery Ngo, chief researcher for Demosisto, Wong and Law's political party.
Increasing support, particularly among young Hong Kongers, for "localist" parties which advocate greater autonomy or even independence from China has also sparked a fiery response from Beijing.
Wang Zhimin, Beijing's chief representative to the city, this week called
for a "zero tolerance" approach to calls for Hong Kong independence, saying there was no room for the idea in China "or in the whole world."
Sunday's march was the second major protest since the jailing of Wong and others
, but while police said around 4,300 people took part, turnout was lower than the tens of thousands who marched in August.
Translating political energy into concrete gains has proven difficult for Hong Kong's opposition, said Lev Nachman, an expert on Asian social movements at the University of California, Irvine.
He compared the Umbrella Movement to Taiwan's Sunflower Revolution, which occurred around the same time, a key difference being that supporters of the latter are now largely in power on the island, while a raft of Hong Kong protest leaders elected to office were swiftly removed.
"Although it was a great victory for Hong Kong activists to have them elected, the disqualification is a large setback," Nachman said.
Chan Kin-man, one of the non-student Umbrella leaders, said this week he was concerned by growing levels of cynicism and hopelessness in the city
, as evidenced by increasing numbers of people migrating overseas
Demosisto researcher Ngo said there were more avenues for the opposition to explore, "not least including the elevation of our democracy endeavor to the international level."
While both the UK and US have expressed concern over the situation in Hong Kong, former governor Patten was skeptical whether countries would risk economic ties with China over it: "I can't pretend that the rest of the world is going to be more heroic than is likely to be the case."
Speaking at Sunday's march, Ng said the opposition camp is facing a "difficult" task, "but when has it ever been easy to fight against authoritarianism?"
Duncan Innes-Ker, Asia regional director for the Economist Intelligence Unit, said the traditional pro-democracy movement "has been undermined by a growing perception that there is no chance of persuading the mainland authorities to allow real democratic reforms."
A major test will come early next year, as by-elections are held to replace the disqualified lawmakers.
"If Hong Kong activists were able to mobilize and elect six localist officials in 2016, there is a chance they can do it again in the next election," Nachman said.
Ng was hopeful that there would be a record turnout for those elections -- as there was for votes last year -- but wary that many protest leaders would be blocked from standing for office, as multiple pro-independence candidates were in the past.
Innes-Ker warned that too many setbacks to the opposition could actually backfire on the government, leading to more radical tactics and greater disruption. "The danger will escalate if (the local government) fails to make progress in addressing the livelihood issues that represent the key cause of public discontent in the territory," he said.