Cunningham has played all 23 matches for the flag favourites this season and is busy preparing for next week's preliminary final, when the Swans will host either Geelong or North Melbourne.
It's been an impressive rise for Cunningham, who had made just six senior appearances over his first two years at the club.
And it was his first experience of the finals last year, when he forced his way into a semi-final win over Carlton and a prelim loss to Fremantle, that drove his marked improvement this season.
"Individually it's been all right, I suppose," Cunningham, who finished eighth in voting for this year's NAB Rising Star award, told AFL.com.au.
"It's come off a big pre-season. After those couple of finals last year, I really set myself to have a big pre-season, and I was able to do that.
"It's still a week-to-week thing, working on my weaknesses and my strengths, just to be able to get a game every week.
"It's massive for me and I'll keep doing that for the rest of the year and the rest of my career."
The 93rd pick in the 2012 rookie draft, Cunningham was a shock selection for the round one clash against the Giants that year, and then spent the rest of his first season in the reserves.
Forced to wait all the way until round 17, 2013 for another senior opportunity, Cunningham made three appearances late last year before he was dropped for the qualifying final against Hawthorn.
Recalled the following week, he kicked his first career goal in the semi-final against the Blues, finishing his two finals with a combined tally of 28 touches and four goals.
The style of those September stoushes prompted the 20-year-old to attack his third pre-season with everything he had – and he hasn't skipped a beat.
Harry Cunningham celebrates a goal during the Swans' clash with Port at Adelaide Oval. Picture: AFL Media
Along with Luke Parker, Tom Mitchell, Jake Lloyd and Zak Jones, Cunningham represents the future of the Swans' midfield.
The pre-season performances of Parker and Cunningham, in particular, moved them past veteran Ryan O'Keefe in the Swans' pecking order.
Adding greatly to his value, Cunningham can fill a number of roles, equally happy lining up forward or in defence.
He also did a masterful run-with job on Fremantle's Stephen Hill in Saturday's qualifying final.
"Harry's a young kid off our rookie list, has played every game and is playing some important roles," Swans coach John Longmire said.
"Whether he's kicking goals off half-forward, he's played wing, he's played inside mid, he's played down back and on the weekend he had a run-with role with Stephen Hill, who's one of the best players in the competition.
"We've got the faith, and the players have enormous faith in his ability, to be able to carry out his role every week.
"He's a superb athlete, so disciplined, and he gives us enormous flexibility."
Flying under the radar entering 2014, Cunningham's form this season has drawn praise from a number of commentators.
Hailing from Wagga Wagga in southern NSW, the birthplace of Swans great Paul Kelly, Cunningham's previous experiences in September have him ready for what lies ahead this year.
"That's what finals are all about," he said. "It steps up a level and the pressure and intensity goes up a level and it definitely did that against the Dockers (last Saturday).
"It took a four-quarter effort to get over them and that's just what it's going to take from now on."
