The Blues have so far recruited 11 new faces this summer with Marlon Pack, Colby Bishop and Dane Scarlett the pick of the bunch.
With his side still in the market on the final day of the window, there’s still plenty of anticipation ahead of the 11pm close.
After the formation of the transfer window in the 2002-03 campaign, deadline day has been well-known to Pompey fans whether it was in the Premier League days with Harry Redknapp or with Paul Cook in League Two.
We’ve taken a look at 10 standout signings who were memorable for all types of reasons - even if it didn’t work out on the pitch!
Here’s what we found.
1. Lomana Lualua
The midfielder joined Pompey in February 2004 on loan from Newcastle before he made his temporary stay permanent later that summer. In total, the fan favourite netted 19 goals in 91 outings for Pompey between 2004 and 2007 - including a memorable double against fierce rivals Southampton in 2005. Photo: Christopher Lee
2. Andy Cole
The former Manchester United striker arrived at Fratton Park in the summer of 2006 on a two-year deal from Manchester City. The ex-England international tipped Pompey to be more successful than the Citizens when he joined from the City of Manchester Stadium. Cole would go on to score five goals in 27 outings before being loaned out later that season. He admitted he should never have joined the Blues. Photo: Chris Coleman
3. Nico Kranjcar
Kranjcar has got a reputation of being a part of Harry Redknapp’s men who used follow the former Blues boss around on deadline day. The midfielder arrived alongside Cole on deadline day in 2006 in a deal worth £3.5m. The Croatian signed a four-year deal at PO4 and went onto feature 100 times, scoring 12 goals. Photo: Clive Mason
4. Andres D'Alessandro
The popular fan favourite spent just half a season on loan at Pompey but is still remembered fondly by the Fratton faithful to this day. His most memorable moment came against Charlton when he netted his only goal for the Blues in 13 games. He returned to Wolfsburg later that summer before joining Zaragoza on loan. Photo: Jamie McDonald