Under Gerad Adams, Roy was part of Sheffield Steelers' 2015 Elite League Championship winning team, repeating the feat the following year under Paul Thompson before being part of the team that won the play-off championship against Cardiff Devils in such memorable fashion in 2017.
But, after defeat to Cardiff at Nottingham Arena on Sunday in a rematch of that play-off final, it left Roy - as well as his coach Thompson - without a piece of silverware for the first time since joining the club.
The popular 31-year-old forward - dubbed 'The King of Sheffield' - finished the campaign as his club's top scorer with 31 goals in all competitions but, for Roy, that is no compensation for the lack of silverware this summer. As is often said, there is nothing worse than losing the final game of the season.
Roy, who led the Florida Everblades to the East Coast Hockey League's Kelly Cup back in 2012, is in the unique position among Steelers' imports from the past campaign of having a year left on his deal.
And, as he spoke in the immediate aftermath of the 3-1 defeat to Cardiff, he has every intention of seeing out that contract. But, following Thompson's mass cull of imports on Monday which saw nine players told they were not being invited back for 2018-19, just who Roy will be lining up alongside when pre-season training camp comes around in August, is anyone's guess.
Regardless, the Canadian is determined to return and ensure that the barren campaign he has just endured is not repeated next time around.
"I didn’t realise initially, but that’s my first season here without a trophy," said Roy. "It’s our goal to win something every year but we came up short this time and we’ll be trying really hard to get it back next year.
"I’m still under contract for next year and Sheffield is my home, that’s where I like to be and I want to come back. I’ve had four seasons here now and I love it here - it’s a great place to play and I like the pressure playing here brings, I like to win, so it’s a good place to be."
WATCH - Highlights of the 2018 Elite League Play-off FinalOn the loss to Cardiff, Roy said the Steelers had gone into the game believing they could repeat the previous year's heroics, particularly after twice coming from two goals down in the previous day's semi-final overtime win against Notitngham Panthers.
"It’s hard to lose that final, hard on the group, especially with the comeback we made on Saturday night against Nottingham," he added. "We went into the final on a high, although we knew it was going to be a hard game against Cardiff - but I think we played a good game.
"Cardiff have had a great year and they are a great team. They won the league, they won the play-offs and it is hard to lose against those guys."