The former Pompey boss has admitted he met some ‘great people’ during his short stint in charge of the club between 2010 and 2011 – a period which was rife with financial problems for the Blues – and was keen for a long-awaited catch-up.
The League One fixture will be only his second time back at PO4 in a managerial capacity since leaving for Nottingham Forest in the autumn of 2011.
He was back just weeks after his departure to the City Ground – a visit which saw his new side suffer a humiliating 3-0 defeat at the hands of Pompey.
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But Cotterill has not been seen in the Fratton Park dugouts since.
Ahead of tonight’s game, the 57-year-old recalled the tough times he experienced on the south coast, with his 2010 appointment coming just one day after creditors voted in favour of a deal to take the club out of administration.
The Blues’ difficulties off the pitch didn’t end there, though, with the club remaining financially challenged and on the brink of liquidation at one point during his time in charge.
It didn’t stop Cotterill leading Pompey to a 16th-place Championship finish in his one and only season in charge, with successive relegations in the years that followed taking the club to the bottom division in the Football League.
And as as he prepared to take on Danny Cowley’s new-look side tonight with fans once again allowed into games, the Shrews boss said he was looking forward to renewing old acquaintances.
Cotterill told the Shropshire Star: ‘Someone said to me the other day that in the four-year spell with me in between it was the only year they hadn’t been relegated, having been relegated just before I got there and afterwards.
‘The club went through an incredibly tough time, certainly when I went there.
‘I remember when taking the job asking "how long would it be before we’re out of administration?” And I was told six weeks – six months later we were still in it.
‘When we did come out of administration the owners that took over put it back in administration.
‘It went through an incredibly tough period for the supporters down there, because it’s them left there all the time.
‘They were incredibly tough times but I made a lot of really, really good friends that I’m looking forward to seeing down there tonight.
‘They were great people through some really, really tough times.
‘Not everybody gets to know how bad it actually was, but you don’t want to say too much and put your old club down.
‘There’s certainly some interesting times I had there as manager under the owners.’
He added: ‘John Westwood will be in the home end with his bell. I’ll be looking forward to that and seeing a big crowd at Pompey.
‘It is a special club down there, I said that at the time and it really is.
‘It’s out on a bit of a limb down there but it is a really, really good football club.’