First, one of them pretended to be a Caucasian man on gay dating app Grindr to lure the victim into agreeing to meet in person.
When they met, Chong Ming Kar and alleged accomplice Iskandar Jantan lied that they were policemen and told the victim to hand over his bag for checks.
But the victim resisted and put up a struggle. Amid the scuffle, Chong dialled 999 and lied on the call that he was a policeman who needed to screen an uncooperative suspect.
Chong, now 29, who had on Oct 6 pleaded guilty to robbery, yesterday received the minimum sentence for the offence - three years behind bars with 12 strokes of the cane.
One count of pretending to be a policeman was taken into consideration in sentencing.
Iskandar's case is still pending and it is fixed for a trial next year.
According to court documents, Iskandar, 42, started chatting with the victim on Grindr last year.
The 27-year-old man cannot be named due to a gag order.
Iskandar and Chong then hatched a plan to lure the victim out so as to rob him.
Iskandar, who had pretended to be a Caucasian man, arranged to meet the victim at a bus stop along Guillemard Road on Aug 25, last year. Iskandar went there with Chong at around 10.40pm that day and waited for their victim.
They cornered the victim when he turned up soon after and told him they were policemen.
Deputy Public Prosecutor Esther Tang said the duo had also planned to threaten their victim by stating that they had something they could use against him.
"Both accused persons thought that this would be effective as gay persons would generally be afraid of having details about their personal lives exposed," she added.
Chong flashed his ez-link card, claiming it was a police identification document, and also shone a torch at the victim. The pair then asked to check the man's bag.
After the scuffle, the man managed to break free and the pair pursued him when he ran away.
When he fell down, the duo snatched his $1,000 Prada bag which contained about $2,000 worth of valuables, including a laptop computer and a wallet.
The man managed to escape in a nearby taxi, and his cousin alerted the police at around 11.50pm. Police arrested Chong and Iskandar the following day. DPP Tang said Chong has made no restitution.
Chong's lawyer, Mr K. Jayakumar Naidu, told the court that his client has a low IQ and "only received $10 and a charger from the whole episode". He alleged that Iskandar had taken all the other items.