Pompey ended their 134-day wait for a victory by defeating Crewe 2-1.
October 20 was the last time the Blues won a match, a 3-1 success over Shrewsbury at Fratton Park.
The club-record wretched run of 23 games without success was finally brought to a halt, though, at The Alexandra Stadium.
During a Patrick Agyemang-inspired first half, Pompey were 2-0 up in the opening 29 minutes.
The on-loan striker scored one and created the other for David Connolly to give the visitors a half-time advantage.
Crewe dominated possession after the break and Mathias Pogba pulled one back in the 63rd minute.
It sparked a nervy finale but Guy Whittingham’s men held on to end their long. long wait.
Pompey were unchanged from the side which drew 1-1 to MK Dons on Tuesday night.
The bench also remained unaltered, with Shaun Cooper still missing following injury and Sam Sodje serving the final game of his three-match suspension.
It took just six minutes for Whittingham’s men to break the deadlock through a quality piece of play from Agyemang.
Walker slipped the ball into the striker’s feet and he held it up with back to goal before cleverly turning and firing in a low shot into the near post corner.
The Blues looked a confident, flowing side in the early stages and, on 22 minutes, a great move down the right saw Connolly slide the ball to the overlapping Jed Wallace.
Wallace produced a dangerous, low ball across the face of goal which Mark Ellis did well to prod past the post for a corner with visiting players everywhere inside the box.
Pompey doubled their advantage in the 29th minute through classy play from Agyemang once again.
Johnny Ertl started it all off with a midfield interception and drove forward before releasing Pompey’s goalscorer down the left channel.
Agyemang forced his way to the byline and clipped a delightful cross to the far post where the unmarked Connolly steered the ball home.
Moments later at the other end, Pogba should have pulled one back only to inexplicably fail to control Ajay Leitch-Smith’s pass when clean through.
On the stroke of half-time, Wallace should have effectively wrapped up the match, only to sidefoot Agyemang’s pass over the bar from around the penalty spot when he should have done better.
After the break, Crewe dominated possession but Ertl dispossessed Pogba to surge forward and unleash a drive which Steve Phillips did well to parry.
Yet the hosts pulled one back in the 63rd minute when Simon Eastwood pulled off a brilliant save to deny Byron Moore and when the ball was knocked back, Pobga stabbed it home from close range.
It was a nervy finish for the visitors, although substitute Reed did strike the right-hand post following a corner.
And after four minutes of time added on, Pompey at last had their win.
CREWE 1 (Pogba 63)
POMPEY 2 (Agyemang 6, Connolly 29)
Crewe: Phillips, Tootle (Mellor 65), Davis, Ellis, Murphy, Pogba, Leitch-Smith, Moore, Robertson, Osman, Aneke (Clayton 46). Subs: Martin, Dugdale, Turton, Ray, Colclough.
Pompey: Eastwood, Moutaouakil, Gyepes, Rocha, Butler, Wallace, Ertl, Racon, Walker (Reed 76), Agyemang (Akinde 86), Connolly (Keene 46). Subs: Smith, Webster, Harris.
Referee: Geoff Eltringham (Durham)