The Portuguese Macao government included gambling as a tax item from as early as in 1848, when the then Governor of Macao, João Maria Ferreira do Amaral, prohibited gambling outside gambling houses or hotels and taxed legal gambling. The Portuguese Macao government gradually incorporated various gambling activities into the monopoly system since the 1850s, including the Fantan game, Lotaria de Vae-seng, lottery, and pigeon tickets, and invited businessmen to bid for their franchise. It was not until 1931 that it consolidated all the gambling activities into a gambling franchise contract known as the “gambling licence”.

Macao’s history saw the emergence of several figures that monopolised the gambling industry, usually referred to as “kings of gambling” by the media. Lou Va-si (or Lou Wa-sio) gained the long-term franchise of a number of gambling activities, such as the Fantan Game, Lotaria de Vae-seng and the Lottery of the Holy House of Mercy in the late 19th century. Although Lou Va-si later committed suicide after his failure in running the Canton Lotaria de Vae-seng, his eldest son Lou Lim-ioc maintained the family’s monopoly of the gambling industry in Macao.

Hou Heng Company headed by Fan Kit-pan made a successful bid to get the first gambling franchise contract issued by the Portuguese Macao government in 1931. However, it closed in three years as the opening-up of the gambling industry in Guangzhou (廣州) and Shenzhen (深圳) at that time dealt a blow on its business. Fu Tak-iam, a gambling operator originally based in Shenzhen, partnered with the Macao businessman Ko Ho-ning to bid for the gambling franchise in 1937. The monopoly of their Tai Heng Company lasted for over 20 years until 1962 when the gambling franchise was granted to Sociedade de Turismo e Diversões de Macau (“Tourism and Entertainment Company of Macau Limited” in English) headed by Stanley Ho Hung-sun, Henry Fok Ying-tung, Yip Hon, and Teddy Yip.

The Portuguese Macao government promulgated regulations of prostitution industry in 1851, marking its legalisation in Macao. According to the regulations, all the brothels must be registered and the prostitutes must undergo an annual medical examination in the hospital. The Inner Harbour area was the major hub of brothels during the late 19th and the early 20th century, with Rua da Felicidade, Beco de Felicida, and Travessa do Auto Novo being the most famous “Three Red-light Streets”. At that time, prostitutes also included singers, dancers, and other entertainers who performed for their clients. The prostitution industry in Macao continued until the end of the War of Resistance Against Japan. It was banned in 1948 and completely prohibited by the Portuguese Macao government in 1954.

Although the Portugal banned slave trade in 1836, Macao gradually became a port for coolie trade from the 1850s. Unlike slaves, these Chinese coolies were indentured labourers who were supposed to have “voluntarily” signed work contracts with their employers. In fact, many of them were kidnapped, heavily indebted, tricked, or forced to do hard labour abroad. At that time, coolies from Macao were mainly sent to Cuba or other parts of South America to work on plantations in place of black slaves, while some got even tougher tasks to collect guano on islands (guano being a valuable fertiliser, and the places where it was collected were harsh, rugged, and dangerous). Many of them died in foreign lands due to overworking from day to night, diseases, and injuries. Some even committed suicide as the circumstances were unbearable. The Portuguese Macao government banned the coolie trade for its inhumanity in 1874, but the dirty trade was still kept alive in secret for some time.