Representing Grimsby against Forest Green in the 2016 National League play-off final, a place in the Football League was at stake.
Bogle had netted the extra-time winner in the semi-final victory over Braintree in front of just more than 3,000 fans a week earlier.
And it was his quickfire double which put the Mariners on the path to Wembley glory.
After a poor start to the game, Bogle rose the highest to head home Jon Nolan’s free-kick to break the deadlock three minutes before half-time.
A minute later, the striker had his second of the afternoon when he reacted first to volley a rebound home from close range.
Bogle was back at the national stadium the following weekend, but suffered a 1-0 loss to Halifax in the FA Trophy final.
Now he makes his return when Pompey face Sunderland in the Checaktrade Trophy final tomorrow.
More than 85,000 fans will be inside Wembley and Bogle is relishing the occasion.
He said: ‘Up until I scored, I was having a stinker.
‘But obviously the goal and what it meant was massive. We went on, won the game and got promoted.
‘Hopefully now I can go there, do it again and lift the trophy.
‘To be fair, when you’re there it’s still mental how it sounds.
‘You wouldn’t have thought only a third of the stadium was full.
‘That was the first time that I had ever been at Wembley at all.
‘It was a play-off final, a massive buzz and it was even bigger when we ended up winning.
‘The most I have played in front of was 55,000.
‘That was at St James’ Park against Newcastle and that was mental.
‘You can’t even hear you and the boys speak, so I can’t even imagine what this is going to be like.’
Bogle arrived at Fratton Park in the final week of January transfer window from Cardiff City for the remainder of the season.
Having spearheaded Pompey’s attack in the past three games, he’s vying to retain his place in Kenny Jackett’s side to face Sunderland.
If he does feature, it will be his first appearance in the Checkatrade Trophy this season.
A hamstring ruled Bogle out of the 3-0 semi-final win at Bury.
And the 25-year-old heaped praise on t he hard work of his team-mates in earlier-round victories, which has has yielded him a third potential Wembley outing.
Bogle added: ‘It’s a big bonus and a credit to the players – it’s their hard work.
‘I haven’t played in run-up to Wembley. I’ve just come in now, so credit to the players.
‘They have beaten some big teams to get here so it’s a credit to the players by how well they have done.’