The midfielder was on the losing side with the Edinburgh club in the 2004 final when Livingston came out on top, but went on to claim the silverware twice while at Rangers.
And Thomson - back at Easter Road for a second spell - says memories of his own past glories will drive him on to what he hopes will be further success this term.
Speaking ahead of Tuesday's third round tie against Stranraer, he said: "I've had a couple of disappointments and I've had highs and, thankfully, the highs in my career have outweighed the lows.
"You never want to think back on the runners-up medals, it's only the winner's ones you remember.
"It would be an amazing feat to get a winner's medal for Hibs.
"Every individual is different. Sometimes people use hurt as a motivation. I use the highs as motivation and how good a feeling it was to win a cup.
"Personally, I've been lucky enough to win a few medals but I'm always striving to win more and to win one for Hibs would be a special day for me and my family."
Hibs have reached the Scottish Cup final in the last two years and Thomson insists the League Cup is also an attractive prospect.
He said: "It's massive. Celtic are always the team to beat, they are always going to be favourites going into the cup competitions and the league competition.
"You always need a wee bit of luck in the cups as well and we want to be in there trying to win it.
"I've been luckily enough to win it twice and playing in cup finals is something you should always dream of and strive to achieve.
"We've got a young squad and we've added a lot of experience into it now and I think we've got a good blend.
"We've got as good a chance of competing for these cups as anyone else."
Hibs picked up only their second three points at home in the current calendar year when they defeated St Mirren in the league at the weekend and Thomson is keen to secure another victory at Easter Road in the cup.
He said: "Results always breed confidence and it was nice to get the monkey off our back with the home game.
"I didn't even realise the home form was so poor but to get a good win was really pleasing.
"We are on a decent run and it's nice to have a cup tie. Hopefully we can keep progressing and get another win at home."