Four former Portsmouth players who raised eyebrows with moves on transfer deadline day

Indeed, four ex-Fratton Park residents were busy making moves on the final day of the January window – moves that raised an eyebrow or two at that.

Take for example Curtis Main’s last-gasp move to League One Shrewsbury.

The 28-year-old striker has had many clubs during his career – but his latest switch arrived after Aberdeen cancelled his contract mid-season.

He had scored three goals in 18 appearances for the Dons this season, with manager Derek McInnes explaining his release by saying he simply wanted to change his forward options.

He told the club’s website: ‘He (Curtis) was a player who worked extremely hard during this time here, but we felt changing up the forward line with different options was the right thing to do at this time.

‘Having worked with him for two years I know how determined Curtis will be to make his next club a success and he goes with our best wishes.’

Main joined Aberdeen from Motherwell in June 2019. He scored seven goals in 41 appearances at Pittodrie.

The forward moved to Pompey from Doncaster for an undisclosed fee in July 2016.

However, he endured a difficult 18 months at Fratton Park, scoring six goals in 23 outings.

Another former Blues striker on the move was David Nugent.

Like, Main, he enjoyed a tough time at Fratton Park, with the former £6m front man enduring a forgettable opening three seasons.

However, the arrival of Steve Cotterill changed his fortunes.

The likeable striker ended up as Pompey’s 14-goal top-scorer at the end of the 2010-11 season – form that prompted a move to Leicester.

The 35-year-old has since had spells at Middlesbrough, Derby and Preston.

But now he can add Tranmere to his long list of Football League clubs during his 19-year career, with the one-time England international joining the League Two outfit on loan until the end of the season.

Speaking of players with a long list of clubs to their name, Nathaniel Mendez-Laing’s deadline day move to Middlesbrough represents his ninth transfer.

The forward, 28, was on loan at Pompey during the 2012-13 season, making eight appearances without scoring.

The Fratton faithful saw glimpses of his undoubted quality, but he’s never really been able to call anywhere home.

Previous club Cardiff seemed to be a good fit, with the former Peterborough man spending three seasons in the Welsh capital.

However, his time at the Championship side was surprisingly cut short on the eve of the season, with Cardiff announcing his departure following a ‘serious breach of contract’.

He’s not played since the Bluebirds’ play-off semi-final against Fulham in July, but former boss Neil Warnock has given him the chance to resurrect his career by bringing him to the Riverside Stadium until the end of the season.

Kieron Freeman is another former Blue whose career was given a boost recently.

He signed for Swindon earlier in the window after being without a club since his summer release by Sheffield United.

The full-back has since played twice for the Robins in League One.

But he sealed a surprise move to promotion-chasing Championship side Swansea on deadline day.

Freeman made seven appearances for Pompey while on loan from Sheffield during the second half of the 2015-16 season.