The following is a list of major crimes in Singapore that happened before 1990. They are arranged in chronological order.
1950s 1950 29 June 1950: Winnie Annie Spencer, a ten-year-old schoolgirl, was found dead at the beach near Labrador Park. An autopsy revealed that she had been raped and strangled to death. 25-year-old Joseph Michael Nonis was arrested and charged with the murder of Spencer. At the trial starting on 24 October 1950, despite having signed a confession, Nonis insisted on going on the stand, where he claimed that he was innocent and that he had been tortured by Chief Inspector J. Rayney, who had forced him to pen down and sign the confession of how he killed Spencer. He also testified he was afraid of Rayney, who was notorious for using torture to extract confessions from suspects during and after the Japanese Occupation of Singapore (one of them suffered from brain damage as a result of the torture). David Marshall, the lawyer who represented Nonis, called in witnesses who had been tortured by Rayney to testify in court. All of Nonis's family members and acquaintances also testified that Nonis was seen at home on the same night when Spencer was murdered, which supported Nonis's alibi defence. A psychiatrist was also called in to assess Nonis's character and the confession written by Nonis. The psychiatrist said in court that such a confession could only be written by an individual of psychopathic behaviour, and Nonis's true character did not fit that of a psychopath. After a trial lasting nine days, in view of the evidence, the seven-man jury found Nonis not guilty of murder and as a result, Nonis was discharged and acquitted of murder. , the rape and murder of Spencer remains unsolved, and the murderer(s) was never found. In the aftermath, Rayney resigned from the police force and he died in 1986 at the age of 82, while Nonis eventually immigrated to England more than a decade later, and finally to Spain, where he lived until his death before 2002. 11–13 December 1950: 13-year-old Dutch-Eurasian girl Maria Hertogh was adopted by Che Aminah binte Mohammad in 1943 and raised as a Muslim under the name Nadra binte Ma'arof. In April 1950, the Hertoghs, through the Dutch Consulate in Singapore, applied to the High Court to regain custody of their daughter. On 1 August 1950, Maria Hertogh entered an arrangement, regarded as a valid marriage from an Islamic perspective, to marry 21-year-old Mansoor Adabi. On 2 December 1950, High Court judge T. A. Brown ruled that the marriage was illegal and awarded custody of Maria Hertogh to her biological parents. The ruling sparked outrage from the Muslim community in Singapore and led to riots that killed 18 people, including police officers and civilians. Hundreds of rioters were arrested, prosecuted and jailed for rioting; nine of them were even given the death penalty for murder. In 1959, after the Malaysian government intervened, the convicted rioters on death row had their sentences commuted to life imprisonment and they were all subsequently pardoned and released from prison.
1960s 1960 April 1960: 49-year-old "Biscuit King" Lee Gee Chong, chairman of the Thye Hong biscuit factory in Johor, was being driven by his chauffeur to his residence in Garlick Avenue when another car forced his car onto an embankment. Three men then pulled him out of his car and into their own and abducted him. Lee Gee Chong was the son of Lee Choon Seng, a former president of SCCCI and chairman of OCBC Bank. Five days after the kidnapping, Lee Gee Chong's dead body was found wrapped in a blanket at a graveyard in Yio Chu Kang. He had died of severe head injuries. It was not reported whether a ransom had been paid and the killer(s) were never caught till today. In July 1965, Lee Gee Chong's son, Lee Boon Leong, was ambushed while he was driving and shot in the shoulder. However, his attackers fled when they saw that he had a gun too. Lee Boon Leong, then in his 30s, survived the encounter. July 1960: 60-year-old C. K. Tang, the founder of the department store Tangs at Orchard Road, was kidnapped outside his bungalow in St Thomas Walk at 7:15 am in full view of children heading to a nearby school. Tang was released four days later after a S$150,000 ransom was paid. One of the kidnappers was Loh Ngut Fong (卢岳鹏), a notorious gang leader who was also behind several other kidnappings in that era. Loh was eventually killed on 11 November 1968 at his hideout in St Heliers Avenue after a seven-hour shootout against police and Gurkha forces.
1961 May 1961: 48-year-old shipping tycoon Tay Kie Thay was ambushed while in his car outside his bungalow at Katong. The gunmen forced his chauffeur out of the car before hijacking it and driving to Broadrick Road, where they transferred to another car. Tay's family paid a S$130,000 ransom but Tay did not return home safely. A few months later, it was discovered that Tay had been shot dead and buried in a vacant plot of land in Tampines. One of the kidnappers, 33-year-old Sim Bin Peng, was arrested and charged with murder, but in the end, Sim was convicted of culpable homicide after pleading guilty, and he was sentenced to seven years in jail in April 1967, and lost his appeal for a lighter sentence in June of that same year.
1963 12 July 1963: The Pulau Senang prison riot occurred at the experimental-type offshore penal colony. A group of 70 to 90 inmates, led by Tan Kheng Ann, started a riot which destroyed and burned everything the inmates had built on Pulau Senang. During the riot, prison officer Daniel Stanley Dutton and his three assistants – Arumugan Veerasingham, Tan Kok Hian and Chok Kok Hong – were murdered by the rioters. About 58 men were accused of murder and rioting; the others received jail terms for rioting. During the five-month trial, David Marshall represented the accused in court. Eventually, 18 men, including Tan Kheng Ann, were convicted of murder and hanged in Changi Prison on 29 October 1965. Another 29 men were found guilty of rioting – among them, 11 were sentenced to two years' jail for rioting while the other 18 received three years' jail for rioting with deadly weapons. The remaining 11 men were acquitted and freed. 27 August 1963: 22-year-old Jenny Cheok Cheng Kid had disappeared in the sea during a scuba-diving trip in the straits between Sisters' Islands. Sixteen months later, her boyfriend, then 24-year-old Sunny Ang Soo Suan, was arrested and charged with murder based on circumstantial evidence such as his eligibility to claim insurance for her death, as well as his strangely calm behaviour towards her disappearance. On 18 May 1965, by a unanimous decision, the seven-man jury found Ang guilty of murder; Ang was thus sentenced to death by High Court judge Murray Buttrose. After failing in his appeals to the Court of Appeal and the Privy Council, and after the rejection of his clemency petition by President Yusof bin Ishak, Ang was hanged on 6 February 1967. Cheok's body was never found.
1964 5 February 1964: 31-year-old Vee Ming Shaw, the eldest son of Shaw Organisation founder Run Run Shaw, was kidnapped at gunpoint at Andrew Road on his way to work. The kidnappers also abducted his chauffeur, 45-year-old Mundari bin Iklal. Shaw and Mundari were released 12 days later after the Shaw family paid a ransom of S$250,000. A total of five youths - Ng Kim Cheng, Low Ngat Yeow, Ooi Chye Kooi, Han Jin Juan and Ng Song Lim (who also kidnapped a rich businessman Ng Quee Lam in another case) - were all sentenced to life imprisonment in June 1966. November 1964: 44-year-old rubber magnate Ng Quee Lam was ambushed and abducted by four or five armed youths when he arrived in his limousine at Kee Choe Avenue to pick up a friend for dinner. A fortnight later, Ng was released after his family paid a S$400,000 ransom. Two of the youths, Ng Song Lim and Wong Tien Soon, were both sentenced to life in prison in June 1966.
1965 10 March 1965: In an incident known as the MacDonald House bombing, three Indonesian marines – 23-year-old Usman bin Haji Muhammad Ali, 21-year-old Harun bin Said and Gani bin Arup – initiated an explosion at the MacDonald House along Orchard Road during the Indonesia–Malaysia confrontation. The bombing caused the deaths of three people – 43-year-old Mohammed Yasin Kesit, 20-year-old Juliet Goh Hwa Kuang and 39-year-old Elizabeth Suzie Choo Kway Hoi – and injured at least 33 people. Gani managed to escape capture, while Usman and Harun were arrested and charged with murder. They were eventually found guilty of murder and sentenced to death by High Court judge F. A. Chua. On 17 October 1968, more than three years after the bombing, the two men were hanged in Changi Prison. In retaliation, 400 students in Jakarta burnt the Singapore flag and attacked the Singapore embassy. Singapore–Indonesia relations improved in 1973 after Singaporean prime minister Lee Kuan Yew visited Indonesia and scattered flowers on the two marines' graves. In February 2014, bilateral ties between Singapore and Indonesia were strained after the Indonesian Navy named a warship after the two marines, prompting Singapore to suspend inter-military relations with Indonesia. Indonesia eventually made an apology but said that it would not reverse its move on naming the warship after the two marines. In response, Singapore accepted the apology and said that it would resume inter-military relations with Indonesia. 15 March 1965: Ian Reed, a soldier with the British Army based in Singapore, murdered his wife, Dorothy Reed (née Campbell). Ian had been having an affair with Dorothy's sister Joan. Ian and Dorothy had a fight, which resulted in Ian losing control and strangling Dorothy to death. Ian then buried Dorothy's body in his backyard in Yio Chu Kang. After Dorothy's death, Joan took on the identity of her sister and moved in with Ian, while everyone else thought it was Joan who went missing, and Ian pretended to help Joan's husband Ismail Omar look for her. This continued for several years. Joan, who knew that Ian killed Dorothy, began to threaten to expose Ian, and repeatedly called Ian a murderer openly. One day in September 1971, Joan exploded in a rage at Ian in front of two friends, repeatedly screaming that Ian was a murderer. This led Ian to confess about the murder to the police the following morning, and police recovered the skeleton of Dorothy in the backyard. On 6 June 1972, Ian was convicted of manslaughter and jailed for 5 years.
1968 5 February 1968: 24-year-old police detective D. Munusamy was stabbed by two men seven times after attempting to arrest their friend under suspicion of being a gang member. Although he was able to wound one of the assailants by shooting him twice, Detective Munusamy was mortally wounded and he died twenty minutes after reaching the hospital. The two attackers, 28-year-old Lim Heng Soon and 29-year-old Low Ngah Ngah were arrested within the next two months and charged with murder. A seven-member jury unanimously found both Lim and Low guilty of murder and the pair were sentenced to death on 30 November 1968. A third suspect, 19-year-old Quek Hock Bee, was initially charged with murder before he received a discharge not amounting to an acquittal. Lim and Low lost their appeals between November 1969 and March 1970, and they were eventually hanged.