Tear gas was fired across Hong Kong as one by one peaceful rallies in seven city districts descended into clashes between police and protesters by early evening.
It was the third consecutive day of violent protest in Hong Kong, a former British colony that is now a special administrative region of China.
The Asian financial hub has been in a state of political crisis since anti-government protests began on June 9, when the government attempted to pass a law allowing for criminal extradition to mainland China.
By 5.30 pm local time, police had arrested 82 people, in the largest arrest of protesters in a single day since demonstrations began.
Clashes also occurred between protesters and other residents.
Earlier on Monday, a car drove into a crowd of protesters in Yuen Long, a district that has seen a number of violent clashes and attacks, and attempted to drive through protester barricades, according to footage shared on social media.
The rallies were held in support of a city-wide anti-government strike called for Monday that saw 27,000 people take annual leave or sick days, according to strike facilitator Save Hong Kong.
The demonstrations were a strong rebuttal of leader Carrie Lam, who on Monday characterised the protests as largely the work of violent fringe groups who were about to "push Hong Kong to the verge of a very dangerous situation."
She said the situation was now threatening the former British colony's status as a semi-autonomous city within China under an arrangement known as "one country, two systems."
"Those ulterior motives are going to destroy Hong Kong and risk 'one country, two systems' to proceed with what they call 'revolution,'" Lam said.
Protests began on June 9 against a now-suspended bill that would have allowed for the extradition of suspected criminals to mainland China.
They have since escalated into an outpouring of anger against the Hong Kong government and Lam herself with hundreds of thousands taking part in marches, flash mobs, and large scale demonstrations.
In recent weeks, protests have turned increasingly violent with residents throwing bricks, rocks and other items at police stations while others have lit trash cans on fire.
Police in return have arrested 420 people since the protests began, a spokeswoman said on Monday. Some 160 rubber bullets and 1,000 rounds of tear gas grenades have been fired by officers in the course of two months, she said.
Lam has failed to meet any of the protesters' demands including that she step down and form an independent commission to investigate police brutality, whose actions she has continued to defend to the media.