However, it is a sixth-round Challenge Cup victory over Wigan Warriors during his time as Hull KR chief that stands out most notably.
The Robins travelled to face the Warriors at the Leigh Sports Village, just two weeks after they had been thumped 60-0 by the same opponents in Super League. Rovers won the fixture 16-12 after Ken Sio’s late try helped them take the spoils.
Chester’s charges headed across the Pennines with a largely-depleted squad, making the eventual triumph all the sweeter for the Wakefield-born coach.
“We only went there with two front rowers and off the top of my head we had about 10 or 11 players missing,” recalled Chester.
“Wigan were littered with internationals, we went there with a little bit of hope and ended up pulling off an unbelievable result. No one had given us a chance.”
With influential half-back Albert Kelly, now playing for KR’s city rivals Hull FC, one of the key men missing, Chester remembers the inspiring performance of captain Terry Campese in the success.
He added: “Terry Campese was unbelievable that night.
“That sticks in my mind and the semi-final when we beat Warrington to get to Wembley, that was another huge performance from us. We didn’t start well, we missed the kick off, it went dead.
“We dropped out and they scored four tackles later. I thought it was going to be one of those days.”
It wasn’t as The Robins triumphed 26-18 at Headingley to book their place in the final at Wembley.
However, the final was one to forget for the East Yorkshire outfit as they were beaten 50-0 by Leeds Rhinos, who went on to win the treble. Chester took Wakefield to the cusp of Wembley the following season.
Trinity reached the last four of the competition but were beaten 56-12 by Warrington Wolves but the Wakefield head coach insists that the trophy is still high on Trinity’s agenda this term.
“It would certainly be nice to get Wakefield there,” he added.
“It is just a fantastic week and a really good atmosphere leading into the final.
“It is certainly high up on our agenda and we will be going all out to win our next game and get into those quarter finals.”
Trinity face district rivals Featherstone Rovers in the sixth round, however there is no date for that fixture with rugby league currently suspended due to the coronavirus outbreak.
The Trinity chief won the trophy as a player with Hull FC in 2005. The Black and Whites triumphed 25-24 in a back-and-forth contest with Leeds Rhinos with the lead changing hands four times at the Millennium Stadium in Cardiff.
He said: “That was an unbelievable experience.
“It is a shame that I can’t remember a great deal about the before and the after, it just passes you by because it happens so quick.
“You don’t get the chance to sit back and go, ‘wow, what an achievement that is.’
“There is a lot of history and tradition with the Challenge Cup and there are a lot of very good teams that have won it.
“I grew up watching Wigan in the late 80s, early 90s winning eight on the bounce.
“It is certainly a competition that I like to be involved in.”
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