Steve Cotterill had infamously bundled Matt Ritchie out the door earlier that year, unconvinced the midfielder was of the required standard to operate effectively in the Championship.
Marlon Pack was another, not offered a new deal by his doubting manager following a miserly seven minutes of league football during his reign.
The home-grown pair scrambled back onto their feet spectacularly.
Scotland international and Premier League performer Ritchie needs no introduction, while Pack is presently in the Championship with Bristol City.
Yet for Cotterill, Webster was different.
A slight central defender from West Wittering, he had been ushered from the Academy into the first-team environment.
Then on August 31, 2011, he represented Cotterill’s Blues side in a friendly at Real Betis.
A crowd of 10,307 were present at the Benito Villamarin when Webster climbed off the bench to replace Lewis Stockford with 20 minutes remaining,
The fixture ended in a 5-1 defeat for the visitors, with Luke Varney grabbing a late consolation.
Webster, however, remained in Cotterill’s thoughts.
Clearly impressed, Pompey’s boss marked him for a bright future, one of the club’s youngsters he would not dispose of.
However, it wasn’t until Michael Appleton was at the helm before the highly-regarded defender would make his league debut – once again as a substitute.
Having turned 17 only 12 days earlier, he was introduced in the second half against West Ham at Fratton Park during a 1-0 defeat.
The date was January 14, 2012, a season when Pompey resided in the Championship.
Today, Webster has amassed 67 appearances and four goals – in addition to a total of eight different managers and caretaker bosses.
Yet never has he been a more settled presence in Pompey’s first-team, establishing himself as a regular in Paul Cook’s promotion chasers.
And having turned 21 earlier this month, he has finally come of age.
Webster said: ‘I suppose I am regarded as a senior pro here nowadays. I have grown up in Pompey’s first-team.
‘Most people come through when they are 18 or 19 or a bit later, but I was chucked in when I was 17 – even earlier than that really when I played against Real Betis.
‘As a centre-half, at that age when you first come into the team, you’re not going to play there because you are not developed enough, you need to be stronger.
‘Michael Appleton told me I probably wouldn’t play centre-half until I was 21, but I never minded playing right-back or left-back, I used to enjoy it.
‘Although, when you end up getting stick and things aren’t going so well it’s not easy, especially when I am naturally a central defender.
‘When you look at the situation now, it’s crazy how quickly things can change and how people’s opinions can alter, that’s football and that’s how it goes.
‘These days I feel very confident, obviously the gaffer has shown a lot of faith in me this season so I have just got to keep performing on the pitch.
‘The other week I turned 21, can you believe that. I’m getting old!
‘I don’t know if I actually feel 21. I have hated every birthday since making my debut because I just wanted to be as young as I could – but now I am 21 I am not really fussed about that anymore!
‘I remember my birthday in 2013 when we played at Walsall and I was right-back.
‘I didn’t like that one either, we lost 2-0 and I didn’t play very well that night.
‘The day before my 21st – on the Sunday – I had a big old meal with all the family, which was nice, a big turn out of about 20 of us.
‘But it’s another day, another birthday.’
Despite Webster’s relative longevity at a club with such a massive turnover of players, it has taken until this season to genuinely establish himself.
At the start of April 2015, the youngster even appeared to be heading out the Fratton exit with his contract nearing expiry.
Andy Awford had nurtured the likeable Webster through the Academy, yet as first-team boss last term he named him only once as a central defender.
Even more concerning for Webster at the time, following a 2-1 defeat at home to Southend, he started only one of the next 15 fixtures, failing to make six squads.
Then Gary Waddock arrived as caretaker manager, a moment which would resurrect the defender’s Pompey career.
Webster was recalled to the side at Stevenage and kept his place for the final four matches of the campaign, with some brilliant displays.
Last summer Cook arrived as boss – with one of his first acts awarding the former Aldershot loanee a two-year deal.
He added: ‘My contract was up at the end of last season and if it wasn’t for the final four matches I would probably be somewhere else now.
‘I have got a lot to thank Gary Waddock for. When Awfs departed he chucked me straight in, gave me the freedom to play and it paid off.
‘At that time for me it was win or bust. I was recalled for Wads’ first game in caretaker charge at Stevenage and thought I played really well despite losing 1-0.
‘That gave me the confidence to move into the next three games and then win a new contract to keep me here.
‘Gary Waddock told me to “Go and play how you like to play” and I think that was what was missing before under Awfs.
‘It was difficult to do that up to that point because I was always in and out.
‘Other central defenders came in, such as Nyron Nosworthy, which I found quite difficult at the time, I wasn’t even on the bench for five games in a row.
‘Against Cheltenham in March I played for 68 minutes and was taken off, it didn’t help to be honest.
‘Then Nosworthy came in. I actually ended up playing a couple of times with Nos and really enjoyed it, he’s a really good guy who had been in the Premier League for most of his career and I learnt a lot off him.
‘Awfs wanted to go with experience. Paul Hardyman rated me highly and a couple of other staff members were saying “Put Webster in” but his decision was to go with experience, which is fair enough because he was in the firing line.
‘Then Gary Waddock put me in straight away – and I haven’t looked back since.
‘When I signed my new deal in the summer I rang him to thank him.
‘He was a really good coach here, all the boys really like him, his training sessions were very good and we got a lot out of him.
‘I still have a lot of respect for him and what he does. I owe him a lot.’
These days Webster is a fixture in the Blues side and regularly lauded by Cook.
The 21-year-old has started 15 of the last 16 matches, his sole absence courtesy of a ban for a Boxing Day red card at Leyton Orient.
With Matt Clarke unable to play against parent side Ipswich in tomorrow’s FA Cup replay, Webster will once again retain his place.
And the man of all ages is revelling in the latest stage of his Pompey life.
He said: ‘I must have seen 150 players since making my debut while there is a new training ground and new facilities, so everything is different.
‘At the end of last season the gaffer had the games watched and decided to keep me on the back of that, so I have a lot to thank him for.
‘I’m really enjoying it, playing regularly in the Pompey team in my natural position.
‘Hopefully I have shown the gaffer what a good player I am and I can keep up my form to stay in his side.’