His last Pompey milestone still makes Gareth Evans wince.
Now the long-serving midfielder is hoping a potential 150th Blues outing this weekend doesn’t result in similar personal humiliation.
Kenny Jackett’s men head to non-league Maidenhead in the FA Cup first round on Saturday, with Evans in the running to feature.
It was July 2015 when the free agent was persuaded by new Pompey boss Paul Cook to undergo a two-day trial.
Almost three-and-a-half years later, the former Fleetwood winger has amassed 149 appearances, 24 goals, the League Two title and the captaincy.
Although the firm crowd favourite is keen not to mark his newest landmark with a sending off.
Evans said: ‘Let’s just hope my 150th, whenever it is, will be better than when I reached 100!
‘It was at Wigan at the start of last season and I had an absolute stinker. I played right-back against Michael Jacobs and had a bit of a nightmare, ending up getting sent off.
‘Luckily we got a point so it could have been worse, but that wasn't my finest hour for Portsmouth to be honest. And coming up against Paul Cook probably made it a little bit harder to take.
‘This is the longest I have spent at any club in my career, so to be on the verge of a 150th game makes me very proud.
‘It means something, it gives you an indication of how you have done at a club and just shows I’ve been doing the right things.
‘I’ve had to reinvent myself a few times. The second year I ended up playing right-back and becoming more of a defender, then I had a spell back on the right wing and next an attacking midfielder for the majority of last season.
‘Now I'm playing as a 10 – but that is what has been needed to get myself in the team. I’ll do whatever I can.
‘There was a spell last season when I was out of the squad and sat in the stands, which was quite tough to take, but it happens in football.
‘I’ve had it before and players are experiencing it now. The door’s not closed on them, you’re not exactly in favour at the time and have to work your way back in.
‘Under the circumstances in which I came down, I never envisaged being here for three-and-a-half years, let alone making 150 appearances. It has been pretty magic ever since I came down.’
Evans’ first Pompey outing was against the Hawks in July 2015.
He scored on his debut in the season’s opener against Dagenham & Redbridge during a 3-0 triumph.
The following season, as penalty taker, he netted in the Notts County promotion game and that memorable title-clinching 6-1 against Cheltenham at Fratton Park.
Evans added: ‘In the summer of 2015, Paul Cook got in touch with my agent and said “Come down and we’ll see what shape you’re in for a day or two. We are looking to sign you so we’ll get all paperwork sorted”.
‘Seven weeks later I was still here without a contract, but ended up signing one in the end!
‘The majority of players the manager signed that summer, marquee players, have moved on and I'm still here, so it’s a bit weird really.’