City of Portsmouth Sunday League side Rovers, who announced before the final they would not be running a team next season, added the PDFA Victory Cup prize to the Division 1 title they won last month.
In an action-packed final, goalkeeper Tony Male saved Kieran Clark’s spot-kick as Milton defeated Jameson Arms 8-7 in a penalty shoot-out that went to sudden death - after 15 successful spot-kicks.
The sides could not be separated in normal time as 10-man Rovers, who saw George Roy dismissed in the first half, drew 2-2 with a Jameson side who were also playing their final game before folding.
Rovers had turned the game on its head late on, with Michael Mollory's header and Aston Leigh's strike putting them 2-1 ahead with just minutes remaining after cancelling out Fred Penfold's earlier second half opener.
However, drama was to follow as substitute Jordan Page volleyed home with virtually the last kick of normal time to force penalties.
It was the teams’ second draw of 2020/21 with last September’s league meeting a memorable encounter as well – Jameson hitting back from 0-4 down in the first half to draw 4-4.
In what was a feisty final that had virtually everything, Rovers' Tyler Moret hammered a 14th-minute spot-kick against the crossbar after Shane Cornish had been pushed to the ground from a corner.
Moret, keen to make up for his penalty miss, got in behind just after the half-hour mark, chipping the onrushing Joe Boxall before Liam Kyle cleared up the danger.
He could only chip back to his goalkeeper, though, who picked up the ball and was punished for a backpass. Striker Dec Seiden was unable to find the net from close range from the resulting free-kick from inside the area, as his goalbound effort was blocked.
Rovers' task was then made all the more tougher 11 minutes before the break when a needless lunge from midfielder Roy saw him shown a second yellow card.
Jameson would make the most of their man advantage on the hour mark, as Ryan Smart's superb pass slipped in an unmarked Penfold who, despite Rovers' offside protests, had no problems firing past Tony Male.
Moret must have been worrying it wasn't going to be his night when the striker's thunderous strike from a tight left-hand angle was brilliantly tipped onto the crossbar by Boxall.
But 10-man Rovers' tenacity was finally rewarded nine minutes from the end. Bognor midfielder Leigh delivered a perfect corner and centre-half Mallory headed home from close range.
The turnaround was complete some six minutes later and Rovers must have thought they'd done enough at that stage. Leigh's pressure paid off as he took the ball off Kyle before keeping his composure to fire home.
There was still time for some late, late drama, though. Defender George Tribble horribly miscued a clearance which eventually led to substitute Page volleying home right at the last to send the Jameson bench into frenzy.
So, in what was both clubs' final act in existence, a penalty shoot-out would decide the final.
It looked as though it would never end, with 15 spot-kicks converted before Clark became the first to miss in sudden-death and Male was Rovers' hero as they lifted the PDFA Victory Cup.
Milton Rovers: Male; Dollery, Willett, Mallory, Taw, Glen, Roy, Cornish, Leigh, T Moret, Seiden. Subs: Gardener, Rimmer, Thomas, Watts, Tribble, M Moret
Jameson Arms: Boxall; Cook, Kyle, Clark, O'Neill, Clements, Knight, Cooper, F Penfold, D Penfold, Smart. Subs: Page, Wilson, Rogers, Kemp.