Craig MacGillivray (1) of Portsmouth applauds the travelling fans at full time during the EFL Sky Bet League 1 match between Bristol Rovers and Portsmouth at the Memorial Stadium, Bristol, England on 26 October 2019.
Nineteen of those have been permanent first-team additions, while 18 have been loans deals. We’ve taken a look at each of those signings to see how those deals have worked out for Pompey. Note: the figure of 37 includes Anton Walkes’ loan deal and his permanent move to Fratton Park.
Proved a huge success at Pompey, playing 78 times over two years. Departed under a cloud in the summer after snubbing new deal. Now at Peterborough.
Left-back arrived on loan from Huddersfield in 2017. Impressed hugely in pre-season but picked up injury on opening day of season and never played for Blues again.
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Joined from Spurs in 2017 on three-year deal. Played 50 times in debut season but hasn't featured since EFL Trophy game against Arsenal U21s in December 2018.
Signed from Ipswich on three-year-deal, Pitman has scored 40 goals in 94 appearances. Scored 24 times in debut season but no longer a guaranteed regular.
Signed for an undisclosed fee from Chesterfield. Injury and illness plagued his two-year stay at Fratton Park. Made 50 apps and scored once before being released in summer.
Former Dagenham & Redbridge striker has made 87 appearances and scored 18 goals following step up from non-league football in 2017. Now seen as a defender by Jackett.
Joined on loan deal from Burton to be Holmes-Dennis' replacement but twisted knee three games into Blues spell. Failed to feature again. Now a regular at Notts County.
Joined on loan from Cardiff but wasn't the goal threat from left-wing that Blues had hoped for. Made 30 apps but scored only three goals. Now at St Johnstone.
Played key role in Pompey's first season back in League One during loan from Cardiff. Returned to Cardiff at end of 2017-18 season but move back to PO4 never materialised.
Left-back featured only twice following January 2018 loan from Wolves. Still at Wolves but currently on loan at Lokomotiv Plovdiv in Bulgaria.
Made 17 apps during loan from Wolves but failed to score a single goal. Also failed to score on loan at Walsall last season. Now on loan at Dunajska Streda in Slovakia.
Signed initially on loan from Spurs before making deal permanent in 2018. Impressed as a holding midfielder but used at right-back more recently. Has made 55 apps but currently out of reckoning.
Joined on loan from Nottingham Forest in January 2018. Walked straight into team but injury on second debut for club ruled him out for the rest of the season.
Winger has played 63 games and scored 15 times following move from Derry City. Enjoyed impressive first campaign. Has been out of form this term but scored in draw at Rovers on Saturday.
Failed to convince Jackett of his Pompey credentials following move from Bromley. Made eight apps in total and scored one goal. Joined Leyton Orient in summer.
Pompey's undisputed No1 following summer 2018 move from Shrewsbury. Has made 71 apps to date. Form has seen him called up for Scotland squads.
A key man in Pompey's engine room, his importance to the side saw him named captain earlier this season. Has made 70 appearance since move from Burton.
Is first-choice left-back following summer 2018 free transfer move from Bristol Rovers. Currently the vice-captain, Brown has made 61 Blues apps to date.
Made 17 apps and scored three goals while on loan from QPR but failed to establish himself in Jackett's plans. Returned to QPR in January 2019. Now at Wycombe.
Proved a huge Fratton favourite during short loan stint from Millwall. His early return to The Den proved a massive blow to Pompey's promotion hopes last term.
Scored five goals in 12 appearances for the Blues while on loan from Aston Villa. Despite never building great momentum, was recalled early by Villa.
One start, no goals and four appearances summed up the forward's loan spell from Wolves. Was sent back early. Now at MK Dons after period out of the game.
Made only two appearances following permanent move from Rochdale last January. Has played 11 times this season but midfielder remains on the fringes of things.
Midfielder has featured only eight times since January move from Shrewsbury. Has been hampered by injury. Yet to play this season.
Scored on his debut at Luton but only found the net three more times while on loan from Cardiff. Now back at Bluebirds, where he's scored one goal this term.
The Wigan loanee failed to score in 11 appearances, although nine of those outings came as a substitute.
Another loanee who failed to have an impact on the second half of last season. Scored one goal in 10 appearances during uneventful spell.
The accompanying picture says it all. The Barnsley loanee failed to make an appearance for the Blues. Now with Swindon.
Brought in as Nathan Thompson replacement the right-back has enjoyed a stuttering start to his Blues career. Has two assists in recent weeks but was dropped after Wimbledon defeat.
Is Pompey's top scorer with five goals this season, but can't establish himself as a regular started. Eight of his 14 apps have come from the bench.
Currently below Burgess and Raggett in the central defence pecking order. Has made 11 apps this term but last league outing was against Burton on September 17.
Injury hampered the winger's Pompey return at the start of the season. Has been used more regularly lately but yet to score in 10 apps.
Has started past six league games after slow start to life at PO4. Steadily improving though. Will be interesting to see what happens when Oli Hawkins returns from injury.
Has started the past two games at right-back despite being signed as a central midfielder. Came with a big reputation but yet to impose himself on Fratton Park.
Showed bags of potential early on after big-money move from Burton but not been at best since recent return from injury. Didn't feature at Bristol Rovers on Saturday.
Has scored three times in 17 apps following move from Doncaster in summer. No doubt front man will have expected more after 67 goals in three seasons at Keepmoat.