Pompey's season of hope ended with the opposite emotion - despair - as Plymouth struck in injury time to end the Blues' hopes of Wembley and promotion.
Peter Hartley's header from a corner was the cruellest way to end a promotion campaign that had looked on track as Pompey dominated their hosts for long spells of the semi-final second leg.
The Blues weren't helped by injuries - key men Gareth Evans and Danny Hollands both hobbled in the first half, Evans after a heavy challenge, Hollands after catching his boot awkwardly in the turf.
For the first 55 minutes Pompey were the better side but gradually Plymouth began to control more of the possession and the home crowd, quiet until that point, awoke accordingly.
Even so the game looked set for extra-time - until Hartley struck a minute into the two added on.
Pompey had thei chances - none better than when a ball into the box fell to the unmarked Ben Close, whose volley was well-hit but too high.
Jake Jervis headed against a post in the 89th minute and it looked like the let-off that had earned Pompey extra-time. Not so.
Plymouth won a final corner and despite Enda Stevens' efforts at the far post, Hartley headed in.
With only a minute or so, Pompey launched one last long ball into the Argyle box but the hosts crowded Pompey out and the dream was over.
Year four in League Two beckons.
Pompey (4-2-3-1): Allsop; Davies, Burgess, Barton, Stevens; Hollands (Close 44), Doyle (c); Evans (McGurk 31), Roberts, Bennett (Chaplin 90+3); McNulty. Subs not used: Whatmough, Haunstrup, Tollitt, Naismith
Referee: Paul Tierney
Attendance: 15,011 (1,696 Pompey fans)
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