Not least of those was Manchester United, whom his Hearts youth side knocked out on route to capturing the prestigious Milk Cup back in 2004. Tomorrow, Annan Athletic await in a Ramsdens Cup semi-final, and although the opposition might not be as seductive, a victory would still be sweet for the Raith Rovers captain.
Thomson was just a fresh-faced 16-year-old then, when he defeated Dublin side Belvedere alongside team-mates such as Lee Wallace, Andrew Driver and player-of-that-tournament Calum Elliot, who has also made Stark's Park his latter-day home. The Edinburgh youngsters had already knocked out Manchester United's starlets, including Darren Gibson and Ryan Shawcross, on their way to a memorable triumph.
Since then, his showpiece experience has been lacking: the full-back was on the books at Tynecastle but not involved in their Scottish Cup wins in 2006 and 2012 - he spent the latter on loan at Raith - and that personal disappointment has stayed with him since. So the 26-year-old is relishing the opportunity to set up a likely final with Rangers, who along with Stenhousemuir make up the final four.
"It's a great chance to reach a final," he admitted. "Since [the Milk Cup] I've played in a few rounds here and there, and I played in a League Cup semi-final [when Hearts lost 1-0 to St Mirren in 2010]. I missed the 2006 Scottish Cup final when there was only myself and Calum [Elliot] involved from our age group.
"And for the 2012 final after I had come back from being on loan at Dunfermline I was sort of frozen out and wasn't part of the plans. So, being here for a semi-final is good. A lot of the boys have never played in a final, so this is a good chance to get to one. It might not be the best cup in the world, but it's still a cup."
With Rangers expected to defeat Stenhousemuir - whom they recently thrashed 8-0 in the league - it would raise the profile of the Ramsdens Cup and make the final a more glamorous occasion, but also make the chances of success all the more difficult.
"Although we're not looking ahead, if we were to get there we would have a great chance of facing Rangers in the final," he conceded. "Most neutrals will be looking at it that way. You know if you are going to win this cup then you are probably going to have to beat Rangers at some stage. So, it was either going to be a good semi-final or the chance of a good final. Hopefully we can get there and give our family and friends a good day out. Wherever it might be held it would be a great honour to lead the team out in a cup final."