This year he has been nominated for the PFA Scotland Player of the Year award after an outstanding premiere season in the country’s top flight.
The 25-year-old striker has scored 13 league goals this term after manager Paul Hartley plucked him from the ranks at Cowdenbeath to sign a pre-contract agreement with the Dens Park club in April 2014.
He is the second top scorer in the Premiership behind fellow-nominee Adam Rooney of Aberdeen, and says it has been quite surreal to go from part-time football to rubbing shoulders with the best Scottish football has to offer.
He said: “It’s hard to take in, especially when all the players in the league have voted for you to be a nominee. I’m just obviously delighted and a wee bit taken aback to be fair.
“Playing against boys like that, they could easily go and play in the English Premier League no bother. There’s Van Dijk scored two free-kicks in a row and Johansen has come over from Norway and he’s flying as well.
“I’m just delighted as last season I was playing part-time football so to get voted in the best four players is unbelievable.”
Stewart could be forgiven for thinking his entire year with Dundee has been a highlight given his meteoric rise. However, he pinpoints the club’s first win in a decade over city rivals United as his favourite moment of the campaign.
The Scottish frontman scored in that game, as well as the other two league matches against Jackie McNamara’s side, but a goalkeeping blunder from United goalkeeper Radoslaw Cierzniak means he didn’t even see his shot go in the net during Dundee’s historic 3-1 win on April 8.
“I had already turned away looking for a foul from the ref,” he said. “I just heard the roar from the crowd, turned back and the ball is in the net, and I just didn’t know what had happened.
“I think it was 10 years since the club had beaten them, so to beat your local rivals, we are all just delighted for the fans as well.”
The Dens Park side surprised many by securing a top-six spot after being promoted from Scotland’s second tier as champions last year.
But Stewart says manager Paul Hartley convinced the squad early on that finishing in the upper half of the table was not beyond them.
“From winning the league last season and coming up, a lot of people were saying we could get relegated again. But the gaffer has brought in a few new faces and the boys have just gelled together.
“We knew we had ability in the dressing room and we’ve always thought about getting in the top-six from day one.”
You can watch Dundee continue their impressive Premiership campaign when they take on Celtic next Friday night in front of the Sky cameras. It’s Live on Sky Sports 5 from 7.30pm