Perry was well aware that Trudeau's father, Pierre Elliott Trudeau, was prime minister at the time, but asserts that it was no reason for animosity.
Perry explained that he and his friend laid into Trudeau because "he was excelling in a sport that we weren't.so it was pure jealousy".
"I'm not bragging about this", he said. "I want to say a special thank you to the permanent representatives who are here tonight". "I think he was the only kid in school we could beat up".
Check out the full segment above. "And we, you know, we beat him up". "This is awful. I was a stupid kid".
Kimmel questioned why Canada provided no security to the young son of the prime minister, joking anyone who tried to beat up U.S. President Donald Trump's son Barron would end up in "the stockades" or "Russia somewhere".
Surprisingly, Trudeau's dad didn't have any secret service members looking after the future Prime Minister, which as Kimmel pointed out, would never happen today.
Perry and Trudeau both attended Rockcliffe Park elementary, a public school located in one of Ottawa's wealthiest neighbourhoods and frequented by the children of ambassadors and politicians.
Mr Trudeau and Ms Trump had met previously when she helped host a summit on women business leaders and entrepreneurs when the Canadian prime minister visited Washington earlier this year.
"The world gets to see what it is to lean on each other and be there for each other through the darkest times", Trudeau said ahead of the performance.
'I think it was rather instrumental in him going to such big heights and becoming the Prime Minister, ' he said.
Trudeau has yet to comment publicly on Perry's story.