He was convicted of three charges, one each for outrage of modesty, sexual assault by penetration, and obstruction of justice.
The second man, 51, who has been friends with the first man for 20 years, was given 18 years' jail, which includes a one-year term in lieu of 24 strokes of the cane.
He was convicted of six charges: two for rape, two for outrage of modesty, one for possession of an intimate image, and one for obstruction of justice.
Under the law, the two men cannot be caned as they are above the age of 50.
The men, who appeared in the dock dressed in suits, cannot be named owing to a gag order. Publishing their names might lead to the identification of the victim as they were part of a small circle owing to their field of work.
In sentencing the pair, Justice Hoo Sheau Peng said it was "appalling" that the two men committed the offences despite their professional standing, reputation and experience.
The judge said the additional jail terms were warranted to compensate for the lost retributive effect of caning.
Lawyers for the two men told the judge that they would be appealing against her decision.
The judge also ordered the two men to pay compensation to the victim, which amounted to nearly $3,700.
The compensation order covered expenses including treatment following the assault and flight tickets for the woman to return to Singapore to assist in investigations.
The woman worked under the first man for more than a year and was occasionally in touch with him.
In February 2023, they agreed to meet for dinner while they were in Singapore.
Her assistant made a restaurant reservation for two at 6pm on Feb 26.
That afternoon, the two men began drinking gin and tonic in the second man's hotel room.
The first man then texted the victim to go up to his friend's room and buy some tonic water on the way.
When she entered the room, she was introduced to the second man, whom she did not know personally but recognised due to his professional reputation.
The woman sat at the edge of the bed as they chatted and sipped on the gin mixture that was handed to her.
The two men then moved to the bed. After she downed a second glass of gin mixture, the conversation turned sexual. She was then served white wine.
After texting her assistant regarding the reservation, she vomited on the bed and lost consciousness. She had patchy memories of her body being violated and saying "no" many times.
She also remembered lying in the bathroom as someone showered her.
At about 1am, she woke up unclothed with the second man on the bed and fell asleep again.
When she woke up again, she found her clothes and two pairs of boxers on the floor. After getting dressed, she checked the bin for condoms to find proof of sexual activity.
She asked the second man why she was naked, and he replied that they helped clean her up after she vomited.
After returning to her hotel, she searched on her phone to find out the legal consequences of rape in Singapore and the number for the police.
When she found out the severity of the consequences, she was hesitant to make a police report as she did not want the first man, whom she considered her mentor, to suffer these consequences.
She later decided to get herself medically examined. A police report was made by KK Women's and Children's Hospital.
The first man, who was represented by Mr Chenthil Kumarasingam, argued that the woman had consented to the sexual activities or that he believed that she had consented.
He testified that the second man and the woman went to the bathroom, and when he checked in on them, he saw them having sex.
He said after the two returned to the bed, the woman reached out to touch his groin, and he carried out a sex act on her.
The second man, who was represented by Mr Eugene Thuraisingam, argued that the woman was conscious at the time but could not remember much of the events due to partial alcohol-induced memory loss.
He testified that she initiated the sexual activities by kissing the two men before suggesting that everyone move to the bathroom.
In convicting the pair on July 22, Justice Hoo rejected the two men's accounts, which she noted contradicted each other.
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24-Sep 2025 Wednesday
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