It was a tumultuous 12 months for the Pompey boss who had to endure more agony than any predecessor.
But in terms of low points, according to Michael Appleton, nothing can top the day Portpin broke their budget promise.
Back in May, owners-elect Balram Chainrai and Levi Kushnir pledged to present the then Blues manager with a £4.5m playing budget for the current campaign.
Appleton prepared accordingly, lining-up a squad of players to fit into that financial structure. But on the eve of the season, Portpin re-evaluated, slashing it to £1.5m.
It forced Appleton to tear up his plans and start again – a moment he is still bitter about.
Ultimately, Portpin were not accepted by the Football League, despite being PKF’s initial preferred bidders.
Yet Appleton still ranks that time as the most despondent he ever got at Fratton Park.
He told The News: ‘There are a few low points.
‘It was not easy straight away, with players not getting paid.
‘Then there was losing the four players on loan – including our captain – having gone into administration and been deducted 10 points.
‘I am not going to forget those kind of things.
‘I think the biggest one, though, was spending all my summer putting a squad together on one budget and then having that taken away from me.
‘The way that whole thing was handled hurt me the most out of everything I put up with at Portsmouth.
‘I was looking forward to putting a squad together to get promotion, regardless of a 10-point deduction.
‘I had spent a lot of time talking to agents, talking to players, lining-up deals to put into place when Portpin were going to take the club out of administration.
‘Then it was wiped from under my feet. They also didn’t get the club.
‘We got on with it as best we could and tried to have a good go, but that hurt.’
For Appleton, though, there were high points.
He added: ‘The highlight was Southampton away. It was a draw but felt like a win.
‘They had a very good team destined to go up to the Premier League.
‘But over the two games they didn’t beat us – and we took two points off them.’