One side on display last night will not be playing in League Two next season, the other will only be escaping via the play-offs.
York’s fate is already sealed, the sad inevitable delayed irrespective of a thoroughly-deserved victory at Bootham Crescent.
As for Pompey, a dreadful first-half showing finally eliminated any remaining hope of automatic promotion.
It will be the play-offs for Paul Cook’s side this season – providing they don’t slip out altogether during the final four fixtures.
The damage was done during a shambolic opening 45 minutes when a Minstermen side without a win in 12 fixtures established a two-goal lead.
It was as bad as Pompey have produced this season, lacklustre, clueless, weak, embarrassing and ultimately the destroyer of aspirations for a top-three finish.
The last time Pompey won at Bootham Crescent was in December 1976 with a 4-1 scoreline.
In recent times there was John Sullivan’s horror show and then a goalless encounter last term – albeit saved by Ryan Brunt’s remarkable late miss.
This was another performance to drain the cheeks of those travelling fans who deserve so much better for their support.
Once Bradley Fewster and Lewis Alessandra netted in the space of four first-half minutes there was to be no coming back.
To make matters worse, Luke Summerfield added a third on 48 minutes.
Gareth Evans did reduce the arrears on 55 minutes, albeit courtesy of some generous goalkeeping from Scott Flinders.
Yet despite the game opening up and the hosts missing many more chances to increase their lead, no other goals arrived.
Crucially for Cook’s men it meant a 3-1 defeat to the League Two strugglers who still require a miracle to remain in the Football League.
And a second-successive defeat not only ends dreams of a top-three finish but now raises questions over whether Cook’s team can succeed in the second choice of the play-offs.
The boss made three changes to the side which lost in such agonising circumstances to Plymouth at the weekend.
Having named the same team for four successive games, two of the alternations were enforced following injuries to Christian Burgess and Gary Roberts.
That meant a first appearance since the trip to Mansfield for Adam Webster – kept out of the side recently by Matt Clarke.
Roberts, who received a nasty blow to the head on Saturday, was last night replaced by Marc McNulty, who operated behind the lone striker Michael Smith.
The change saw Evans restored to the right-hand side of the attacking four, ending Adam McGurk’s run of four successive starts.
It was a first start in six matches for the nine-goal midfielder, who has been an impressive contributor during his maiden Fratton Park campaign.
McGurk dropped to a bench which featured returns to the first-team squad for Ben Tollitt, Adam Barton and Kieron Freeman, while Ben Close dropped out completely.
With only a minute on the clock, Ben Davies swung in a dangerous ball from the right which somehow eluded all his team-mates.
Seconds later the right-back popped up to hurl himself in front of Josh Carson’s shot and deflect it for a corner – only for the referee award a goal-kick, much to the disgust of home fans.
There were cheers when a corner was awarded on four minutes down the right.
Summerfield took it but it came to nothing.
Pompey won their first corner in the sixth minute when Smith’s through ball – intended for the run of Evans – was diverted out by a York foot.
The Blues were beginning to enjoy possession of the ball and on 13 minutes a Kyle Bennett corner narrowly failed to find the lunge of Clarke, with it put behind for another set-piece.
Yet Paul Jones was called upon to make the first save of the match on 15 minutes when Luke Hendrie fed Fewster down the right channel and the striker’s powerful angled shot was parried behind for a corner.
Jones then had to stop Summerfield’s free-kick from wide on the left, with a linesman’s flag for a foul preventing a York player following up.
However, the hosts did break the deadlock on the half-hour mark following a right-wing Summerfield corner.
Scot Bennett headed the delivery back across goal and there was Fewster at the far post to nod home, despite Jones’ best efforts to keep the ball out.
Barely four minutes later and Alessandra doubled York’s lead when he prodded home Hendrie’s excellent cross from the right after a quick break.
There was a rare threatening moment from the visitors four minutes before the break when Bennett cut inside and drove a right-foot shot over the bar from the edge of the area.
On the stroke of half-time, there were concerns when Webster fell to the floor with no player around and was swiftly replaced by Barton.
Barton’s second touch saw him head Summerfield’s shot off the line after Jones had beaten away a cross from the right as further damage was prevented in first-half stoppage time.
There were no changes at the break – yet within three minutes it was 3-0.
The ball came to Summerfield 30 yards from goal and he struck a sumptuous right-foot shot which rocketed into the top corner to give Jones no chance.
Pompey responded with Evans’ ball down the left allowing Smith to get ahead of his marker, only to curl a right-foot shot wide of the far post.
Evans then pulled one back on 55 minutes when Smith laid the ball off to him and a first-time left-foot shot was fumbled into his net by keeper Scott Flinders.
In their very next attack, Davies’ cross from the right was met with a powerful header from McNulty which was tipped around the post by Flinders – yet the flag was up for off-side.
On 64 minutes, Summerfield was booked for a foul on Bennett and from the free-kick Davies curled a shot narrowly wide.
Moments later Tollitt was introduced for Bennett and his first touch was a shot which was blocked before his right-foot follow-up fizzed over the bar.
The game was proving an absorbing affair and Fewster and Summerfield then both went close to restoring York’s three-goal advantage.
On 74 minutes Cook made his final substitution with the out-of-sorts McNulty replaced by Conor Chaplin.
Still Pompey pressed to find a way back into the game and Tollitt saw his delivery from the right cleared off the line by the covering Hendrie.
Yet it was the hosts who finished the stronger as Cook’s side pushed forward and they finished with a fully-warranted 3-1 success.