The January window is always an ominous thought for many Pompey fans, with multiple first half of the season successes hampered by winter window failures in recent seasons.
We take a look at the worst XI from January signings over the past five years.
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1. GK - Lewis Ward
The goalkeeper arrived on loan at Fratton Park in January as back-up to first choice keeper Craig MacGillivray following the loan departure of Alex Bass. However, during his six month stay on the south coast he failed to make an appearance between the sticks, appearing 23 times on the bench last season.
Photo: Jason Brown
2. CB - Aaron Simpson
Simpson is probably more well known around the Pompey fanbase for his recent appearance on ITV's Love Island in the summer. Highlighted by Paul Cook to help the Blues’ right-back woes, he arrived on deadline day but failed to appear in the starting XI during his six-month stay on the south coast.
Photo: Joe Pepler
3. CB - Charlie Daniels
The former Bournemouth full-back arrived with a massive reputation on the south coast following a successful spell at Shrewsbury in the first half of last season. Although making 18 outings last campaign he was full of mistakes, costing Pompey a play-off place. After time in the Premier League he failed to live up to expectations set to him by Pompey fans.
Photo: Alex Burstow
4. CB - Sylvain Deslandes
The Wolves loanee arrived at PO4 in January 2018 in Kenny Jackett’s first season in charge. Deslandes made two appearances in blue which came against Rotherham and Gillingham as Jackett tried to overcome his left-back issue.
Photo: Joe Pepler