Nearly six years on, Tommy Smith is still getting over the crushing blow.
A career that had seen three failed FA Cup semi-finals finally conjured up the showpiece event the hard-working winger had been so desperate to experience.
Suited and booted, Smith headed for the Wembley changing rooms with visions of playing his part in a famous Cup final upset.
But while Avram Grant’s administration-hit, relegated Blues side pushed double winners Chelsea all the way in a spirited 1-0 defeat, former England under-21 international Smith remained a spectator.
And the abrupt manner in which he learned of his May 2010 match-day omission still pains the recently-retired 35-year-old.
He said: ‘I am just getting over it now.
‘It was bitterly disappointing and, to be brutally honest, it wasn’t handled very well by Avram Grant.
‘I turned up at Wembley and was heading into the changing room when he pulled me to one side and told me there and then.
‘I had 30 family members in the crowd who thought I was going to be on the pitch and I had to wander over in my suit and give them the bad news
‘I was seething.
‘The problem at the time was that we had a few injured players coming back.
‘Jamie O’Hara had been out for two months but decided he was going to play, as a few others did.
‘And to make things worse, I don’t think they were all fully fit, either, which stuck in the throat.
‘That was a tough time for me.
‘It wasn’t the best way to end the season.
‘Relegation and administration was hard enough, but with that on top on a personal level, that was very tough to deal with.’
Forced to sit behind the bench and watch on as his team-mates did battle, Smith admits his memory of what might have been a career highlight was tarnished.
‘There were a couple of other lads left out as well so we just sat behind the bench,’ he said.
‘To lose as well in the fashion that we did made it quite a tough day all in all.
‘We gave a really good account of ourselves and on another day we could have lifted the trophy.
‘It was great to be part of the experience and brilliant to get to the final – I had lost three semi-finals in my career before that.
‘It was a double-edged sword because it was a great day for the club but my memory has been tarnished a little by the situation.’
Sadly for Smith, his FA Cup final omission was not the only time his nose was put out of joint in the competition – literally.
In a cruel and ironic twist of fate, the energetic attacker was denied another possible Wembley appearance when he suffered a broken nose in a Premier League 5-0 defeat to Chelsea.
That came just two weeks ahead of a semi-final showdown with Spurs as Smith – who opened his Blues scoring account in a rare league win over Hull the previous weekend – was left to reflect once again on what might have been.
He said: ‘I had worked really hard in training to force my way into the team under Avram and I had started to make a few inroads.
‘But then I had my nose broken against Chelsea which set me back two or three weeks – it coincided with the semi-final as well which was really frustrating.
‘I was on the bench, which was great, but Avram stuck with the team who played the week before and I wasn’t in that so it was very disappointing.’
While many would forgive Smith for reflecting on an eventful one-year Blues stay in a negative light, it wasn’t all bad news for the ex-Hornets attacker.
His sole Pompey goal, netted at Fratton Park against Hull, is a moment he is able to cherish – even if it was a case of too little, too late.
‘Being in and out of the side, sometimes you just need the ball to fall to you and knock it in – then you are away,’ said Smith.
‘For me, though, it didn’t quite happen until late on in the season.
‘It was nice and such a relief to get the goal – I’ll never forget that.
‘In truth, I felt I really should have had a better return for the games I played in.
‘But that’s the way it works out sometimes.’
It’s fair to say things didn’t exactly go to plan for Smith from the start of his south coast spell.
Having left financially-troubled Watford in a £1.8m switch to the then Premier League Blues, he was seen as a key piece in Paul Hart’s Pompey puzzle.
But the great expectation that surrounded Sulamain Al-Fahim’s summer purchase of the club soon unravelled into chaos.
Results on the field stuttered, with a seven-game losing streak to begin the new campaign worsened by off-field uncertainties as the money dried up.
Players and staff alike failed to be paid as Smith saw firm admirer Hart lose his job a matter of weeks after arriving.
He added: ‘It was out of the frying pan and into the fire a little bit!
‘The issues weren’t nearly half as bad at Watford as what panned out at Portsmouth.
‘Things fell apart pretty much as quickly as they came together.
‘As much as it was no excuse to the season and how things panned out, the financial concerns didn’t help matters.
‘The change of managers didn’t help either, neither did the amount of loan players we had.’
That said, Pompey’s impressive run to the FA Cup final convinced Smith that the Blues’ assembled squad could have stayed in the Premier League, before a nine-point deduction for entering administration decided their fate.
He said: ‘Without a shadow of a doubt we had the quality to stay in the Premier League, as our run to the FA Cup final showed.
‘But there was such an influx of players and we had a real diverse dressing room with a lot of french-speaking players.
‘Again, not that that is an excuse for on-field results, but we needed a strong manager to pull everything together and that didn’t quite happen.
‘Standards slipped a bit and the change of managers and all of the ongoing off-field stuff just affected us more than it should.’
With Grant waving goodbye to relegated Pompey following their Chelsea loss, many of the club’s squad followed suit.
Smith stayed the summer and indeed started the first few games in the Championship for the Blues before he was sold to divisional rivals QPR – a move that brought about an immediate and surreal Fratton Park return.
With Pompey winning 1-0, Smith won and converted a last-minute penalty against his former club, much to his own disbelief.
He said: ‘To return to Fratton Park so soon after leaving was very surreal – it was only the second or third game I had played at QPR.
‘It was very odd to come back and to get that last-minute penalty.
‘It wasn’t even a penalty – it was a really harsh decision.
‘I remember looking around at all of the players at QPR and thinking: “I can’t take this”.
‘Someone gave me the ball and nobody else wanted it – in the end I was happy to take the penalty.
‘I didn’t celebrate the goal because I thought it best not to.
‘I know some people think it’s ridiculous and you should celebrate your goals but as a player I think it is a nice touch.
‘I respected the club and the fans and wanted to show that.’
Smith retired from football in the summer, bringing an end to a distinguished career.
He has wasted no time in pursuing other interests, though, with a blossoming second career in real estate under way.
He said: ‘I own estate agents now – I have five offices local to where I am in Watford.
‘I bought my first one a few years ago and have just gradually been growing it.
‘Since I retired I have jumped into that – I love it.’
TOMMY SMITH ON...
...UNFULFILLED ENGLAND AMBITIONS
I was 17 when I broke into Watford’s team and played for England under-18s and then the under-21s for a little bit – at that point I did think the future could hold a possible senior cap.
When I was young some of the big clubs were showing a bit of interest in me so playing for England was certainly something I thought about.
But with the way my career progressed it was something I realised probably wasn’t going to happen.
To score for the under-21s was great, though – it was the sixth goal in a 6-1 thrashing of Georgia.
It’s something that’s nice to have on the CV and to get on the scoresheet for my country is something no-one can take away from me.
...POMPEY’S ‘SHAMBOLIC’ USA TOUR
I have never been on a trip like it and I have been on some really shambolic ones with football clubs at different levels!
I remember Steve Cotterill just arguing the whole trip – either with hotel staff over a lack of rooms or airport desks over cancelled flights.
It was complete carnage.
...HIS LOVE OF CRICKET
I grew up playing a lot of cricket and I try to play as much as I can in the summer.
My dad played to a really good standard so it was sort of forced on me as a youngster.
Not many footballers like cricket, though, they think it’s boring or a load of rubbish!
But I love watching the Ashes, especially when the whole country gets into it.