Rupert Chester Inglis Watson was the twelfth child of Walter Watson and Maria Inglis. According to newspaper reports related to his death, Rupert became a paperboy at the age of ten, and then at about 13 he followed in the footsteps of his maternal grandfather, David Inglis, and went to work for a bakery in Coburg. After working there for a short time, he left and went to work for the Victorian Railway Commissioners as a painter's apprentice at the Newport workshop.

On Easter Thursday, 16th April 1908, Rupert travelled by train to Ballarat on a free pass he had received as part of his employment. While the reason for his trip is not certain, it is likely it was to visit members of his mother Maria Inglis's family living there at the time. He then returned to Melbourne on the 7.15pm train on the evening of Easter Monday 20th April. The train was due to have arrived at Sunshine station at 10.30pm, but was running late and was still there at 10.49pm when a train from Bendigo, itself delayed, smashed into its rear carriages.

Rupert was one of 44 people killed in the collision, all of whom were on the Ballarat train. He was 15 years old. From information contained in newspapers reports and the Coroner's Inquest we know that his body was one of seven that remained unidentified on the Tuesday afternoon and was transferred from the temporary morgue set up at Spencer St Station to the Melbourne Morgue, where his sister Mary Maria Watson finally identified him on the Tuesday night. The following report of his death appeared in the Coburg Leader:
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The case of the youth, Rupert Watson, of Drummond street, Coburg, who was killed, was particularly sad. It appeared that the lad's father and brother had died during the last 12 months, and that his widowed mother was nearly beside herself with grief at the loss of another son - more especially as another brother was just stricken down with fever and had to be removed to the hospital. The funeral took place at the Coburg Cemetery on Thursday afternoon, the Rev. Mr. Lloyd conducting the funeral service.

(The Coburg Leader, Saturday 25 April 1908, p. 1)
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Rupert was buried with his father (and later his mother) at Coburg Pine Ridge Cemetery. A funeral notice in the newspapers indicates he was a junior member of the Independent Order of the Rechabites.

In the months after the accident, the Railways Commissioners refused to pay compensation for those killed or injured who were travelling on free passes. Rupert's mother, Maria Watson, was prominent in engaging a solicitor to challenge this position, and eventually was successful in being awarded £300, which was paid by the Victorian Government.