Shannon Keating pleaded guilty in the Frankston Magistrates' Court on Wednesday to a single charge of fraudulently obtaining payments.
He was convicted, fined $5,000 and ordered to repay $103,316 in compensation payments.
The court heard Keating was off work and received weekly compensation payments for two years after surgery for an ankle injury and associated psychological injury.
Keating claimed he injured his ankle jumping from a work truck at a drilling job at Mill Park in August 2016.
However, in August 2018 Keating's employer discovered he was actually injured jumping a bush on a dare during a night out with colleagues, who initially supported the claim that he had been injured at work that day.
Separately on Thursday, Lisa Watt pleaded guilty in the Dandenong Magistrates' Court to a single charge of fraudulently obtaining payments.
She was convicted, fined $2,500 and ordered to repay $28,670 in compensation payments and pay $1,500 in costs.
The court heard Watt ceased work as a hairdressing teacher in October 2019 after lodging a successful claim for a psychological injury.
An investigation later found she had worked more than 100 shifts as a support worker through an online platform between November 2019 and May 2020, earning more than $18,500.
During this time, Watt had submitted nine certificates of capacity declaring that she was not engaged in other employment.
WorkSafe's Insurance Business Unit Executive Director Roger Arnold said there was no excuse for the dishonesty shown in both matters.
"It's made quite clear that workers' compensation is there to support those injured at work and can't be used to supplement other income, including for work obtained through online platforms," Mr Arnold said.
"Fraudulent behaviour undermines the entire scheme and WorkSafe will not hesitate to make an example of anyone looking to cheat the system for personal gain."
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