The month of May in the 2019–2020 Hong Kong protests saw a resurgence of protests. This was partly due to the containment of the coronavirus pandemic, with a total of less than 50 newly reported cases, and a small uptick in cases at the end of the month. These were the first major protests erupting since early March. Tensions increased again as police employed heavy-handed tactics including towards minors and journalists.

The Hong Kong and Macao Affairs Office (HKMAO) issued aggressive statements about the protesters on 6 May. This was seen by pan-democrats and international observers as a sign that Beijing would increase its level of intervention in Hong Kong affairs; previously on 13 April, both the HKMAO and the Hong Kong Liaison Office had issued strongly worded statements regarding the stalling tactics of the democrats in the Legislative Council.

On 21 May, plans for the promulgation of a national security law for the city by the Chinese government became public. These plans were condemned by pan-democrats as hollowing out the semi-autonomous status of Hong Kong. The protest against the national security law on 24 May was one of the last street demonstrations of the 2019–2020 protests.

Events 1 May An application by the Hong Kong Confederation of Trade Unions to hold its traditional Labour Day march was rejected by police due to the COVID-19 pandemic in the city, in spite of the HKCTU having pledged to adhere to physical distancing rules in force, such as marching in groups of four.

At least 1,500 shops and restaurants participated in an online campaign called "Hongkonger's 5.1 Golden Week", part of the yellow economic circle movement. Organizers said the campaign was intended to keep afloat businesses supportive of the pro-democracy movement, which had been hard-hit by the shortfall in the number of visitors from the mainland over the long May Day weekend due to the pandemic.

Some protesters initiated a "sing with you" event at 7:30 pm in the atrium of New Town Plaza. There were a large number of police cars and riot police on patrol outside the mall. Protesters already chanted slogans and displayed slogans on different floors at 7:30. However, several police officers of the Criminal Investigation Department entered the fourth floor and subdued nine citizens, causing dissatisfaction from bypassers. The policeman warned those present that they were insulting the police. The protesters in the atrium shouted slogans again, with the activities generally being peaceful. By 7:00 pm, nearly 500 riot police rushed into multiple floors of the mall and drove and subdued the protesters on the grounds of violating the "restriction order", causing the shops to shutter their entrances. The police's occupation of the shopping mall was criticized by the citizens and district board members as illegal and unreasonable. The police announced that 11 people had been issued a "restriction order" in the shopping centre throughout the day. Among them, a citizen known under the nickname "Domineering Brother" was twice charged by the police.

A spokesman for New Town Plaza said that the management office did not make the report to the police, emphasising that the police had full authority to enter the shopping centre to enforce the law. However, it did not respond to whether the police notified the person in charge of the mall before entering the scene.

5 May

At about 7:00 pm, about 50 protesters started to sing "Glory to Hong Kong" at Tuen Mun Town Plaza. Before the event, a number of plainclothes policemen asked to see the identity cards of a number of citizens in the shopping mall atrium, and used a loudspeaker to call them to disperse. Then they pulled up a blockade on the top floor. By 7:27 pm, a large number of riot police officers entered multiple floors of the mall and pulled up the cordon. Some shops began to close. Police officers also used the mall broadcasting system to warn the public of violations of the "restriction order". At about 8:00 pm, the riot police withdrew to the outside of the mall and district councillors asked the police and security to explain the reasons for the closure. During this period, a plainclothes police officer was hit with a water bottle. Riot police entered the mall again to disperse the protesters. By 9:15 pm, several Tuen Mun district councillors including Tsang Chun-hing, Kawai Lee, Sam Cheung, and Alfred Lai Chun-wing were subdued by the police on the fourth floor platform. The district board member later said that after discovering that the police had broadcast in the mall, he asked the management staff to explain to the security control room on the 4th floor. At 9:45 pm, a boy holding a drink was suddenly subdued and stopped by multiple riot police officers. The blind lawyer Miss Lu was also taken into the blockade, causing public dissatisfaction. At 10 o'clock in the evening, riot police returned to the mall again, and 4 women and 1 man were subdued. During the operation, the police issued a ticket to 1 man and 5 women.

6 May The Hong Kong and Macao Affairs Office (the top Chinese political office responsible for Hong Kong) released a statement calling protesters a "political virus" and stating that while many in Hong Kong have sympathy for the protesters, "the more sympathisers the tyrants have, the greater price Hong Kong will pay". It also stated the Chinese government has responsibility for safeguarding Hong Kong against the threat. Some remarked the virus rhetoric seemed similar to Chinese communist party discourse regarding the mass detention of Uighurs.

In the evening, citizens started another "sing with you" event in the 1st atrium of +WOO (previously Kingswood Ginza mall). From about 6 o'clock in the evening, a large number of riot police officers were deployed in the area outside the mall. By 7 o'clock in the evening, participants were waiting in the shopping mall atrium and fence location, singing the song "Glory to Hong Kong" and shouting protest slogans. At about 7:30 in the evening, a number of uniformed police officers entered the mall and used the loudspeaker to warn the people gathered at the scene of the violation of the restraint order and demanded that they disperse peacefully within 20 minutes, otherwise they might be charged. After that, riot police officers entered the mall repeatedly, cordoned off the area, and charged four men and women for violating the restriction order. Some people charged were criticizing the police for arresting people and claimed they were being abused by police officers. District Councillor Lam Chun witnessed a protester being kicked by a riot police officer, as a result asked to see the commander to see what the protester did wrong, and was then arranged to take a witness statement at the police station.

8 May From about 12:30 a.m. to 1:00 a.m. in the early morning, there were about 20 people armed with knives, hammers and shovels trying to "clean up" a Lennon Wall on a bridge leading from Lok Fu Plaza to Wang Tau Hom Estate. A few people nearby tried to stop them by shouting at them and it became a conflict. The pedestrians were attacked. After a while, the police arrived but when the attackers tried to escape by taxi, the police didn't stop them. At the end, 10 people were arrested, including at least 3 being attacked. Three Wong Tai Sin District Councillors suspected that the police purposely let the attackers go.

During the lunch hour, some protesters gathered at IFC Mall, shouted slogans, and sang "Glory to Hong Kong". The police showed up, warned the protesters, and subsequently issued some HK$2,000 social distancing fines. Some journalists said they were pepper-sprayed by the police.

9 May At 7 pm, some protesters initiated a "sing with you" demonstration at Plaza Hollywood in Diamond Hill and Tai Po Mega Mall in Tai Po. At Plaza Hollywood, a large number of police vehicles were deployed, and dozens of riot and plainclothes police officers were stationed at the exit of the MTR station. The protesters gathered in the atrium of the mall to chant and sing slogans. By 7:30, a large number of riot police officers entered the mall, pulling cordon lines and dispersing the protesters in the atrium. Citizens waiting outside restaurants in the mall were also required to produce an identity document. Legislative Councillor Jeremy Tam, Wong Tai Sin and District Council Members Carmen Lau and Leung Ming-hong were on the scene observing the police. They were also stopped by police officers, pointing out that they and the people around them violated the restriction order. Tam said that they had only 6 people and that they did not know each other and had no common purpose. A middle-aged man in blue clothes was surrounded by police officers because he allegedly said, "There is no problem with black police buying white powder. Are there any problems with singing?". Riot police officers left the mall at 9 pm. By 10:30 in the evening, two men and a woman were suspected of being recognized in plain clothes and were stopped at the entrance of the shopping mall near Lung Poon Court. One of them was searched for the Liberate Hong Kong banner. After being stopped, the men and women were released and said that they suspected that they were the organizers of the event, and they did not rule out a "restriction order" ticket control based on the information later.

In Tai Po Mega Mall, many protesters gathered and chanted slogans in the atrium of Area C, while riot police officers patrolled outside the mall. By 7:37 pm, riot police entered the Tai Po Mega Mall to disperse the protesters and set up a blockade line. Some protesters walked to Tai Po Plaza to continue chanting slogans. Police officers at the flyover outside Tai Po Plaza warned people in the mall that they had violated the "restriction order". At 7:57 pm, when riot police abruptly rushed into Tai Po Plaza and there was a group of 5 people passing by the mall, two of them were stopped by a group of police officers and then taken away by the police. The police pushed and drove reporters off the scene. At 9 o'clock, the police stopped a number of young people at the footbridge leading to Sun Hing Garden in Tai Po Centre.

10 May Protests on this day were reported to be the largest in months, with 236 arrests in total, for offences including unlawful assembly and possession of weapons. An unauthorised march from Tsim Sha Tsui to Mong Kok was thwarted by heavy police presence. A 12-year-old boy and a 16-year-old girl, who were covering protesters gathering at Tsim Sha Tsui's Harbour City mall while wearing press vests, were briefly detained. Police later said that the pair had not been arrested and been released without charge or warning. Later, protests shifted to sing-along events at several shopping malls. Early in the afternoon, police were suspected to have fired a pepper ball inside MOKO Mall of Grand Century Place in Mong Kok to disperse protests. Later, some protesters attempted to set road blocks, with some debris set alight on Sai Yeung Choi Street South. At around 8 pm, over 100 riot police officers suddenly rushed the crowd at Sai Yeung Choi Street South and deployed pepper spray, hitting at least one person and several reporters. Among those arrested was Democratic lawmaker Roy Kwong, who was alleged to have thrown a water bottle at officers, an accusation that Kwong firmly denied. He was treated in Queen Elizabeth Hospital for neck injuries that he had sustained during his arrest.

The Hong Kong Journalists Association alleged that abuse and insults of reporters had taken place during the protests on that day, with HKJA chairman Chris Yeung Kin-hing stating that pepper-sprayed reporters had been denied immediate treatment and that, contrary to internal police guidelines, some reporters had their bags searched and been told to turn off their cameras.