Having arrived from Newcastle Knights, it was in his first season in the UK with Leeds that the Australian prop won it for the first time as they famously went on to complete the treble in 2015.
Cuthbertson lifted the Cup again with Rhinos at Wembley last year but - now aged 36 - has since moved to start playing part-time with York, the ambitious Championship club who host Wigan Warriors in the third round tomorrow night.
“It will be really good for the club, especially being at that new stadium, and to get a Super League team there with such a history like Wigan as well,” said the front-rower, who has started working for Preston Baker estate agents in the Minster City.
“It’ll be great to have Wigan in town and I’m sure they’ll enjoy the experience over here in York.
“On top of that, it will be really good for us to see where we are as a club and how we compete with Super League teams.
“It was disappointing last week to lose like we did against Toulouse but they are a good team especially when you see the names they have on paper there.
“But Friday will be another really good test. Everyone wants to win; everyone wants to get to Wembley.”
Having won away at Sheffield Eagles and London Broncos to reach the Cup third round stage, York were brought back down to earth with a bump when they lost their Championship opener 21-6 against Toulouse on Saturday.
However, they are looking for a response on Friday and, although massive underdogs against Adrian Lam’s side, have plenty of players with Super League experience in Cuthbertson, Danny Kirmond, Ryan Atkins and Ben Jones-Bishop.
Moreover, Kieran Dixon and Liam Salter were in the Hull KR side that lost to Cuthbertson’s Leeds at Wembley in 2015 while James Green was 18th man plus Australian stand-off Brendan O’Hagan has proved a fine recruit from Canberra Raiders.
On his move to York, Cuthbertson said: “It’s been good.
“They’ve been very welcoming and we’re enjoying living in the area.
“We’re not far from the city centre and I’m working here too so it’s been nice.
“I’m working for Preston Baker real estate agents so I’m doing some nine ‘til five work nowadays!
“It has been tough, if I’m honest. It’s just getting that balance between work, rugby and family life but I am enjoying it.”
On the field, Wigan will provide a formidable challenge given their rich seam of international quality including England internationals John Bateman - back from Canberra where he recommended York to O’Hagan - Zak Hardaker and Liam Farrell.
Cuthbertson played alongside Hardaker for 18 months at Headingley including that 2015 success.
“Zak’s been playing brilliantly this year which is great to see,” he said, about the former Man of Steel who is excelling at full-back again after a drugs ban in 2017.
“He’s such a talent is Zak and it’s great to see him find a home at Wigan.
“And there’s Brad Singleton there, too, who I spent five years with in the front-row at Leeds.
“It’s good to see them having a really good dig over at Wigan and performing really well.”
Cuthbertson marks his 300th game on Friday with more than half of those appearances (157) coming in Leeds colours and having also represented Newcastle Knights (53), St George Illawarra (19), Cronulla Sharks (12), Manly (54) and New South Wales City (two).
“I can’t even believe it’s my 300th,” he said.
“The only way I knew is that my mum messaged me to tell me! God knows how she found out…!
“I can’t believe it’s come around so quickly.”
Asked for his recollections on his first game, the two-time Super League Grand Final winner said: “My debut was for Manly against Cronulla Sharks in 2006.
“And all I remember from it - aside from the win - was getting a proper hospital ball and being absolutely cleaned out by the opposition front-rower Hutch Maiava!
“I’m glad I survived through that week let alone make 300.”
Maiava, of course, went on to have a brief spell in Super League with Hull FC the following year.
Cuthbertson’s stay has been far more longstanding - and the Challenge Cup, in particular, holds fond memories for him.
“It’s outstanding,” he said.
“Growing up in Australia we don’t have that competition - such an historical Cup and one where basically you get to win or you go home.
“That is quite exciting for myself.
“I’ve always loved the Challenge Cups and had a couple of good runs in it which probably makes it even more exciting for me going into this Wigan game.
“But I’m just as excited about the possibility of playing in the 1895 as well. We’ve a lot to look forward to in the upcoming weeks.”
The 1895 Cup is the knockout competition for non-Super League clubs that was introduced in 2019 when Sheffield Eagles were the inaugural victors.
The lower division sides that reach the Challenge Cup third round - this year being York, Featherstone Rovers, Swinton Lions and Widnes Vikings - play semi-finals in June for a second chance of getting to Wembley.
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