In a week in which the Shamrock Park club lost a double appeal against Irish Football Association disciplinary measures, hopes appeared high for an on-pitch boost.
The Ports held control until the final moments as Crusaders grabbed goals on 86 and 87 minutes to turn the tables.
Marcio Soares marked his return to Shamrock Park by breaking the deadlock on nine minutes with a close-range finish off Ross Holden’s run.
However, the Ports managed to level the tie within minutes thanks to Eoin Kirwan’s measured pass that found Aaron Haire in space.
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Haire steered a shot past Michael Dougherty - one of three former Portadown players in the Crusaders side alongside Soares and Michael Gault.
Haire enjoyed success again off Kirwan’s pass when, on 40 minutes, he created space with a slick turn and curled home his second of the night.
The Ports pushed the lead to 3-1 as Richhill-born teenager Zak Wilson celebrated his first start of the season with a teasing free-kick delivery that Haire flicked on then Stephen Hughes forced home.
The frantic first-half play continued with a second goal for the visitors within seconds as Michael Carvill’s cross was steered past goalkeeper Chris McGaughey by the unfortunate Mark Carson.
Crusaders pressure after the break failed to test the Ports lead - with one Carvill shot drifting low across the face of goal and past the post.
However, late drama featured goals by Heatley and Carvill to send Crusaders marching on.
PORTADOWN: McGaughey, Carson, Rodgers, Breen, Oman, Garrett, Wilson, Kirwan, Hughes, Haire, Simpson. Subs: Larkin, Henderson, Parker (Hughes, 85), Withers, Ferris (Simpson, 90).
CRUSADERS: Dougherty, Burns, Gault, Coates, Mitchell, Soares, Cushley, Holden, McClean, Clarke, Heatley. Subs: O’Neill, Carvill (Holden, 34), Forsythe, Owens (Soares, 72), Snoddy (Cushley, 67).