Barnoldswick Town boss Danny Craig enjoyed unprecedented success as a coach at the Arbories alongside Steve Wilkes and Steve Cunningham as Padiham were promoted to the Evo-Stik League.
However, the former Stork became the final corner of that managerial triangular to lose out in the final of the Macron Cup.
Wilkes was the first to suffer, losing 2-0 eight years ago when Runcorn Linnets boss, before Cunningham's Colne had the silverware swiped from their clutches by Atherton Collieries last year.
But Craig's was the most heart-breaking defeat, by some distance, as nine man City of Liverpool prevailed after penalties to secure the treble.
Coral's non-league team of the year had already secured promotion from the 10th tier of the football pyramid, winning the First Division play-offs, while adding the Reusch Cup.
And they added another trophy to the cabinet in a quite outstanding first season for the club as Town failed to score their final spot kick.
Town gifted their opponents an early advantage in the tie when defender Jonathan Hodgkinson upended Joseph Camozzi inside the penalty area.
Referee Lewis Smith didn't hesitate for a second, pointing to the spot to spark a cacophony of noise from the City of Liverpool supporters.
Matthew Williams stepped up to take responsibility from 12 yards out, stroking the ball to his right hand side and sending Jordan Gidley the wrong way in the process.
Danny Craig's side failed to impact on the final inside the first 20 minutes but a good chance for Mark Threlfall seemed to galvanise the Hallmark Security Premier Division outfit.
The striker pressed Daniel Dalton and Allen Weston midway through the half, forcing the central defensive pairing in to an error.
However, with almost too much time to think, Threlfall opted for a delicate finish, making it too easy for Stephen Longrigg to stick out a leg and turn the ball around the upright.
Town, growing in confidence and looking more convincing in possession, went again just before the half hour mark.
Liam Blades collected a crossfield pass from Jake Lloyd, moved in to space down the right hand side, supplied the cross, but Threlfall glanced wide when getting across Dalton.
Town didn't look like they were in any need of a helping hand at that point but there were given one with just four minutes of the first half remaining.
Goalscorer Williams went from hero to zero when recklessly taking Harry Thompson out on the left flank before kicking out at the midfielder when grounded.
Incredibly, the winger seemed the only person on the pitch to look surprised when the red card was brandished.
Town almost made their numerical advantage count immediately. Zack Dale whipped in the resulting set-piece but, with Longrigg caught in no man's land, Hodgkinson somehow flicked wide of the post when towering above John Connoly at the far post.
Dale was involved again as half-time approached, doing well to manufacture space inside the box and shifting the ball on to his right boot but Kevin McEllin got across well to divert the shot over the bar.
Town, as expected, had the bulk of the ball after the break and probed for the equaliser. After Threlfall cleared the crossbar from just inside the penalty area, Craig made a change to get extra bodies forward as Aaron Hollindrake replaced captain James Crorken.
And that transformation paid dividends with eight minutes of normal time left. Thompson and Dale were inventive with a short corner before the latter guided the ball across the six-yard box for substitute Hollindrake to tap home from close range.
Town had their chances to win it as Town's goalscorer poked over the bar, taking Threlfall's cushioned header first time despite having the space to take a touch.
Dale also went close, slicing wide of the upright with his right boot when slightly off-balance, before Connoly drilled in to the side-netting at the opposite end.
Aching muscles and fatigue seemed to play a part in extra-time as Town ran out of ideas. City of Liverpool sat back, soaking up any pressure by cutting off passing lanes and forcing their opponents to go long.
Simon Burton's side had it spot on tactically, countering Town well to create numerous chances in the additional 30-minute period.
Elliot Nevitt looked odds on to score when nodding the ball past Gidley from a percentage punt forward but Hodgkinson just about did enough to recover and force the substitute wide.
Fellow substitute Daley Woods also found himself clear on goal soon after when Connoly survived the linesman's flag to thread the ball through but the former Padiham man stung the legs of Gidley.
Nevitt had the final chance of the tie when ghosting beyond Town's backline and breaking in to the box but once again Gidley saved with his legs.
A second bookable offence for a late challenge on Lloyd saw Kevin McEllin given his marching orders but Town didn't have enough time to capitalise.
That brought the lottery of a penalty shootout. The scores were locked at 1-1 after three spot kicks as Nevitt and Threlfall converted while Weston and Francis Foy were denied by Gidley with Longrigg foiling both Andrew Hill and Dale.
Woods and Hollindrake were both successful to make it 2-2 but Shaun Airey's decisive spot kick clipped the bar after Connoly had netted to crown City of Liverpool champions.