Ebou Adams fired the Blues to all 3 points at Fratton Park with a late goal in front of the Fratton End.
Portsmouth almost came away with just the solitary point after Zak Swanson’s stunner and Adrian Segečić’s close-range effort were cancelled out by 10-man Sheffield United in the second half.
The first win in 4 Championship matches takes John Mousinho’s side up to 16th in the table and with now 11 points out of a possible 27.
Mousinho made 3 changes to the side that started in Sunday’s South Coast Derby.
Adrian Segečić, Iyad Mohamed, and Marko Milovanović came into the XI, while Tyrese Shade was absent from the squad and was replaced by Ben Killip.
Portsmouth had a bulk of possession over the 90, as the Blues moved the ball from back to front to make things happen.
Tom Cannon did have chances to give the Blades the lead, despite Pompey controlling most of the first phase, but the Ireland international could not find an opener.
Ryan Kavuma-McQueen showed a threat on the left flank, but it was his partner behind him on the left in Zak Swanson who got the evening going.
Swanson initially whipped a ball into the six-yard box, which was nodded away by Patrick Bamford and then cleared by Sydie Peck, whose clearance was intercepted by Swanson.
And then the Blues number 22 fired a curling effort from around 25 yards out into the top left-hand corner of Michael Cooper’s goal to make it 1-0, 41 minutes gone.
Then the already booked Hamza Choudhury, who originally gave that free-kick away, was given a second yellow card when he later clattered into the Kavuma-McQueen.
HALF-TIME: Portsmouth 1-0 Sheffield United
Madiodio Dia burst away on the counter-attack after intercepting a United throw-in, and the Senegalese defender found Kavuma-McQueen through on goal and one-on-one with Cooper, but the former Plymouth shot stopper denied the teenage winger.
Kavuma-McQueen kept posing all sorts of issues for Chris Wilder’s side, and the Chelsea loanee eventually helped Pompey double their lead 54 minutes in, as he teed up Segečić at the front post, who tapped the ball home to make it 2-0.
Wilder’s side did pull a goal back though just five minutes later, when the Blades' captain Japhet Tanganga got ahead of Mohammed to slice in Tahith Chong’s ball.
And then the warning lights came on for Pompey, when ten-man Sheffield United found an equaliser via Cannon, who nodded in Kalvin Phillips' corner to the front post.
Mousinho made a triple change, with Abu Kamara, Mohammed and Swanson coming off, and Keshi Anderson, Adams, and Terry Devlin coming on with 20 minutes to go.
Despite testing Cooper straight away amid his arrival to the pitch, Anderson had to be taken off just 18 minutes after coming on, as Odin Bailey played the final 8 minutes of the night.
Pompey then won it very late on, as Segečić's bobbled cutback across goal fell to Adams, who thumped the ball past Cooper to win it for Portsmouth with one of the last actions of the 90, before the five minutes of added time that the Blues held on for.
FULL-TIME: Portsmouth 3-2 Sheffield United
Portsmouth: 1. Schmid (GK), 22. Swanson (24. Devlin), 5. Poole, 55. Dia, 16. Meghoma, 37. Mohammed (38. Adams) 7. Pack (C), 11. Kamara (14. Anderson) (27. Bailey), 10. Segečić, 25. Kavuma-McQueen, 29. Marezi (9. Bishop) (Formation: 4-2-3-1)
Unused subs: 31. Bielica (GK), 30. Killip (GK), 19. Shein, 32. Kenny
Goals: Swanson 41’, Segečić 54’, Adams 89’
Bookings: Meghoma 27’, Schmid 60’, Adams 82’
Head coach: John Mousinho
Sheffield United: 1. Cooper (GK), 8. Choudhury, 5. Tanganga (C), 15. Kitching, 3. McCallum, 7. Rothwell (4. Arblaster), 42. Peck, 19. Chong (11. Donovan), 45. Bamford (25. McGuinness), 22. Brereton Díaz (27. Phillips), 9. Cannon (23. Campbell) (Formation: 4-2-3-1)
Unused subs: 17. Davies (GK), 10. Ayew, 14. Burrows, 26. Oné, 44. Riedewald
Goals: Tanganga 59’, Cannon 67’
Bookings: Choudhury 44’ (second yellow card), McCallum 60’
Manager: Chris Wilder
Referee: Oliver Langford
Venue: Fratton Park
Attendance: 18,446 (including 583 away fans)
The Pompey Live: Extra-Time podcast from tonight's broadcast at Fratton Park is also available to listen back to!
Jake and Graham will be back on Friday (October 16th) night's episode of The Football Hour alongside Blues fan Brendan Tuttiett to further reflect on this match and also preview Saturday's (October 17th) match for Pompey against Norwich City at Carrow Road.
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