Not since Karl Connolly scored twice to send the Blues crashing out of the FA Cup in 1997 have I been so downcast after a derby.
Back then as a 14-year-old from Blacon I was probably too young and too cocksure to know better.
To know that in football there's no divine right to win matches or even reach a certain level of performance.
Karl Connolly broke my heart that night but as teenagers do, I got over it pretty quickly.
Now some 19 years later I've reached an age where I can certainly be considered old enough to know better.
Yet in the wake of the 3-0 defeat at the Racecourse on Saturday afternoon I felt that same gut-wrenching disappointment, that same teen angst from December 1997.
I know it'll pass and ultimately it's a game of football which in the grand scheme of things matters little but it still hurts. A lot.
The facts tell us the odds were stacked against the Blues from the start.
Wrexham have bigger gates and bigger commercial revenues ergo a bigger budget, which should equate to a better squad.
Little confidence could be taken from Chester's record on the road this season, four league wins - three against teams below them - from 18 games while the Dragons went into the match unbeaten in eight and with the incentive of knowing defeat would effectively end their play-off challenge.
But history suggests the form book and such handicaps matter little on these occasions; throw them out of the window along with rhyme and reason.
Being honest, I didn't expect much from the game. The negatives have far outweighed the positives this season so it was difficult to have much faith in the Blues having a good day.
The opening 10 minutes set the tone: Tony Thompson saving from Robbie Evans before Jamal Fyfield and Connor Jennings fluffed good chances.
Wrexham dominated the first-half with Lee Fowler running things in the middle of the park and Kayden Jackson's pace stretching Chester's defence time and time again.
Credit to Thompson, Ben Heneghan and Ryan Astles for managing to repel the threat for so long but it always felt a case of when and not if the resistance would give.
Chester compacted the midfield after the break and it worked to an extent. However, the limited threat the Blues posed in attack had now gone with Wrexham keeper Rhys Taylor untested in the second period.
The penalty decision and dismissal of Astles was of course central to the outcome but it would not be right to describe it as a turning point, it was the breaking point.
With an extra man and a goal to the good, the Dragons began to enjoy themselves and as well they might because the second and third goals were far too easy.
Chester's young side had managed to keep themselves in the contest for an hour but the sending-off and Wrexham's first goal exposed their fragile confidence, setting up a final 20 minutes that was frighteningly one-sided.
Had the Blues somehow managed to hold on for a draw we would probably be praising a backs-to-the-wall performance and a valuable, hard-earned point.
But for me, as a fan first and foremost, I'm not sure that's much to celebrate.
There's no question Wrexham are on an excellent run and have significant momentum and of course budgets have to be taken into consideration.
However, these are Chester's fiercest rivals and a team in the same league not a division or two above and maybe some of that teenage ignorance of practicalities and logic remains but I expected more.
Saturday was the biggest winning margin in a cross-border derby for 41 years. Blues fans have had to put up with some rotten teams in that time but none have been swept aside with that ease in such an important fixture.
No-one likes losing, especially in derbies and especially not 3-0, but feeling at least that you've given it a good crack helps with the acceptance.
In the context of this season, the biggest concern is how much damage the defeat has done to the squad's frame of mind.
With teams below them closing the gap, the Blues realistically need a minimum of four points from the Easter fixtures with Barrow and Guiseley.
That would give them the opportunity to reach the 50-point mark with a win over Boreham Wood on April 2 and avoid a nerve-shredding end to the campaign.
If and when that has been done the inquest into this season can be opened but for now survival must be the focus as failure to make the most of these next three games will leave them in serious danger.
There are eight games to go and another seven points should be enough to guarantee another season in the National League and, hopefully, the chance to seek vengeance against Wrexham.
Saturday's defeat has achieved something I didn't think possible and banished Karl Connolly from my mind and for that I suppose I should have a modicum of gratitude.
I take some solace in knowing that, like that FA Cup nightmare in 1997, the pain will subside when the natural order is restored and the bragging rights are reclaimed, but unless Chester can move on quickly from the derby ordeal that could take some time.
