As a player with Hull FC, he lifted the trophy in 2005 following a major shock against Leeds Rhinos and he has plenty of experience of forcing unexpected wins.
Granted, his current side are bereft of numerous star players this afternoon but he is not ready to look for excuses before kick-off against the Super League leaders; far from it.
“We’ve got a game-plan and we need to try and stop their big guys,” said Chester, about opponents who have lost just one of their 17 games so far this term.
“But they all seem to have come back this week. Luke Thompson has been named and Louie McCarthy-Scarsbrook while Mark Percival is back as well.
“With Alex Walmsley, Dominique Peyroux and Zeb Taia, we know how they will come at us.
“We probably do need a bit of luck but, more than anything, we’ll need to just throw the ball around and not die wondering.
“That’s the main message coming from me.”
For those doubting Wakefield’s credentials – they are still missing Dream Team duo Tom Johnstone and Bill Tupou and could give a debut to teenage centre Jack Croft – Chester remains defiant.
Furthermore, he has good reason to feel capable of reaching tomorrow’s semi-final draw.
Chester, 40, explained: “We had a similar situation in 2015 when I was coach at Hull KR.
“We got to the final but in the quarters we went over to Wigan and no-one gave us a chance.
“We lost Albert Kelly during the week, there was no Darrel Goulding and it was all hands on deck.
“Anyway, we ended up turning Wigan over and playing a really good game at Leigh Sports Village.
“Anything can happen in the Challenge Cup and we know that.
“We could have Lee Kershaw and Jack Croft going up against Mark Percival and Tommy Makinson.
“But I’m confident we’ll be ready to give a good account of ourselves and take the game to them.”
Wakefield – who lost narrowly to Catalans Dragons in Liverpool – hope to be bolstered by the return of veteran half-back Danny Brough after he missed seven weeks of action with a hand injury and his game-management quality will be critical.
Admittedly, with winger Kershaw – recently turned 20 and who only made his own debut last month – still working his way in the professional sport, Trinity’s rookie players will surely be targeted.
On Croft, Radford added: “He’s a good young centre.
“He played on the wing for Yorkshire Origin and then for England Academy.
“He’s a real good talent and we’ve got him signed for a couple of years.
“He’s gone really well for our Under-19s. Obviously, this is a really massive step up for him but I’m confident in him if he does get the chance to play.”