Chester - who was sacked two weeks ago - took charge of Wakefield in 2016, the year after what remains Trinity’s most recent win over their nearest rivals.
Willie Poching got off to a flying start as caretaker-coach when Wakefield defeated high-flying Warrington Wolves in his first match at the helm and there were more encouraging signs in Trinity’s performance at the Jungle but, in the end, it was the same old story.
For the 16th successive derby, Castleford came out on top, thanks, in the main, to a blistering start and dominant first-half performance.
On the back of their first win at St Helens in the summer era, the home team got off to a flying start, leading 12-0 after as many minutes and 23-6 early in the second half.
At that stage it was all very routine and Castleford appeared to be cruising towards a third straight win to maintain their hopes of climbing into the Super League play-offs.
But the second period became a mirror image of the first as Trinity, showing great spirit and belief, climbed off the floor to make a real game of it.
They were the better team over the final 30 minutes, scored two unanswered tries and were a hair’s width away from snatching what would have been a sensational victory in the final seconds.
With five points between the teams, a last-gasp kick caused panic behind Castleford’s line, but was scrambled dead before an attacker could get a hand on the ball and the final hooter sounded to prevent the drop-out being taken.
It was a fast-paced contest of thrills and spills, played in difficult conditions.
Both sides will take positives from it: In Castleford’s case the win and way they played in the opening 50 minutes; for Trinity the effort shown during their second-half fightback.
The one disappointment was the attendance of just 4,987.
The 7pm Saturday kick-off, on a very wet evening, will not have helped, but even so, fewer than 5,000 watching a fierce derby, between two teams on the back of a very good win, was a worrying indication of the problems facing Super League as the competition attempts to get back on its feet following the pandemic.
Tigers retain the Adam Watene Trophy, in memory of the forward who played for both clubs and died, aged only 31, in 2008.
He would have enjoyed the aggressive nature of the game, which included a double sin-binning in the first half when rival numbers sevens Danny Richardson, of Tigers, and Mason Lino were banished for 10 minutes following a set-to. The penalty went to Wakefield, but Lino was perhaps fortunate with the colour of card shown after appearing to lash out with a foot.
Richardson had an eventful evening, also providing the final pass for two of his side’s tries, landing two conversions and a penalty and booting a drop-goal on the stroke of half-time to give Castleford a psychologically important three-score lead.
The half-back had a difficult start to the year and was left out of Tigers’ Challenge Cup final side, but is now playing some good rugby. With eight minutes left, he split the Wakefield defence and the game would have been put to bed had Niall Evalds - whose passing also created two tries - been able to hang on to the off-load with the line open.
In the first half Castleford were relentless and clinical on attack and dominant defensively.
Halves Gareth O’Brien and Richardson controlled matters and linked well with full-back Evalds, on the back of a powerful effort up front, particularly from Nathan Massey, Oliver Holmes and Jesse Sene-Lefao.
Greg Eden and Holmes scored the first two tries and, after Wakefield had got off the mark, Derrell Olpherts added a third.
The second period began in similar fashion with Eden racing over for his second touchdown, but then the wheels came off the home side’s express.
Wakefield made too many errors in the opening 40 minutes and didn’t really get to grips with the speed of the contest.
Once they had gone 17 points behind they found the belief to get on the front foot and, with Lee Kershaw running strongly out of backfield, Jacob Miller and Lino kicking well and the likes of David Fifita and Matty Ashurst making big metres up front, they were agonisingly close to snatching the win.
Their three tries all came from kicks, by different players.
Tinirau Arona touched down from Brad Walker’s grubber in the first half and Tom Johnstone - with an excellent finish - and Kershaw did likewise after Miller and Lino had put boot to ball in the final quarter.
Castleford Tigers: Evalds, Olpherts, Mata’utia, Turner, Eden, O’Brien, Richardson, Griffin, McShane, Millington, Holmes, Sene-Lefao, Massey. Subs Watts, Blair, Hepi, Matagi.
Wakefield Trinity: Jowitt, Kershaw, Arundel, Senior, Johnstone, Miller, Lino, Fifita, B Walker, Arona, Ashurst, Pitts, Tanginoa. Subs Kay, Battye, Batchelor, Green.
Referee: J Child (Dewsbury).