Hong Kong police used water cannon for the first time Sunday, raising the stakes against protesters who have staged sometimes violent rallies that have rocked the city for the past three months.
Officers were also seen with drawn sidearms as protesters clashed with police in the district of Tsuen Wan after a rally at a nearby sports stadium.
The financial hub has been gripped by mass rallies that were initially against a proposed extradition bill to China, but have spun into a wider pro-democracy movement targeting the pro-Beijing government.
As thousands of people marched in the pouring rain to Tsuen Wan, a group of hardcore protesters erected makeshift roadblocks and dug up bricks from the pavements.
After firing tear gas in an attempt to disperse the crowds, police drove water cannon vehicles onto the streets, unfurling signs warning protesters they would deploy the jets if they did not leave.
The jets were later fired from the moving trucks towards a crowd of protesters who ran away, but hardcore group of protesters later threw bricks and Molotov cocktails in violent confrontations with riot police.
There were no immediate reports of injuries.
Police had previously said the vehicles, complete with surveillance cameras and multiple spray nozzles, would only be used in the event of a "large-scale public disturbance".
Throughout the protests, Beijing has used a mix of intimidation, propaganda and economic muscle to constrict the protests in a strategy dubbed "white terror" by the movement.
The MTR - the city's metro - is the latest Hong Kong enterprise to face public censure, after appearing to bend to Chinese state-media attacks accusing the transport system of being an "exclusive" service to ferry protesters to rallies.
On Sunday the MTR shut stations near the main demonstration area in Tsuen Wan, in the second day of station closures in-a-row.
"However bleak our future is, we're trying to express ourselves rationally," said Peter, in his 20s, before the clashes began.
"We have faith in ourselves and we have faith in our city that some day our demands will be answered."
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