Sergey Aleksandrovich Shipilov was born on May 17, 1959, in Arkhangelsk, Russia. He grew up in a working-class family and had one sister who was two years younger than him. When he was just seven years old, his mother passed away. After her death, Shipilov said that his father began to bring women and alcohol into their home.

During his early years, Shipilov completed secondary special education. After finishing school, he served in the army. Following his military service, he got married and had three children. For his job, he worked as a foreman in a vocational school where he taught students how to drive. His co-workers viewed him positively, and this led him to have access to an official car, which he could use at his own discretion.

Sergey Shipilov began committing murders in 1995. The first murder occurred when he robbed and killed a woman. He did not confess to this crime until 2016. In 1996, he escalated his crimes, starting a series of rapes and murders. While driving his truck, he picked up a woman. He claimed that she agreed to have an intimate relationship while he was drunk. However, he killed her by stabbing her multiple times, and the knife broke during the attack. He was afraid that she would tell his wife, so he buried her body near Arkhangelsk's brickworks.

That same year, he killed two more women in similar ways. In one case, he struck a woman on the head. He buried their bodies in the Primorsky District, where they remained undiscovered until after his capture. Later in 1996, Shipilov committed another rape. The victim managed to escape and reported him to the police. He was arrested, and during this arrest, police found a bead from one of his victims in his car. In total, he faced charges for eight more rapes that year. He was convicted in January 1997 and sentenced to eight years in prison but was not connected to the murders at that time.

While in prison, Shipilov exploited the prison's system that allowed convicts some freedom of movement. In 1998, he was rewarded for good behavior by being allowed to drive a honeywagon, a truck used for collecting waste. On December 8 of that year, he killed a woman named Doilnitsyna. Unlike his previous victims, he did not bury her body; instead, he covered it with branches. After fearing discovery, he later buried the body.

Shipilov continued his crimes in 1999. He killed a woman on May 16 and another a week later. He buried both bodies at a dump site. Between June 11 and June 27, he murdered four more women, including two young girls. Later, he admitted that he felt pity for the young virgins he initially targeted, leading him to switch to middle-aged women instead. He killed his final victims in September.

All of Shipilov's murders were methodical. He picked up women on deserted roads and removed the interior passenger door handle, making escape impossible. He often offered his victims vodka while driving and killed them when they refused. In interviews, he stated that he believed his victims were prostitutes and claimed he let women who refused drinks leave unharmed. However, evidence showed he forced alcohol on them.

Despite an ongoing investigation into disappearing women, the investigation team could not connect Shipilov to the crimes until it was noticed that his honeywagon passed by the locations where women went missing. He was detained, and after some time, he expressed suicidal thoughts. He eventually confessed to twelve murders and nine rapes, detailing how he killed his victims and revealing the locations of their bodies. He claimed he murdered for the sake of committing crimes rather than any sexual gratification.

On October 25, 2000, the Arkhangelsk Regional Court convicted Shipilov of multiple murders and rapes. He received a life sentence due to the moratorium on the death penalty in Russia. The Supreme Court of Russia confirmed his sentence.

In May 2016, Shipilov confessed to additional crimes. He admitted to two more murders from 1995 and 1996. His punishment from these confessions was added to his existing life sentence. Experts speculate he might reveal more crimes during his time in solitary confinement.