He has featured in the World Cup finals, the Premier League, Dutch football and amassed more than 450 appearances, scoring 182 times.
But now David Connolly has been backed to ‘surprise’ League Two defences in the forthcoming season.
The evergreen striker will be lining-up in the bottom division for the first time in a much-travelled yet prolific career.
Despite having turned 36 this summer, Pompey fans will testify his age is an irrelevance.
Perhaps not so the opposition. May they underestimate at their peril the danger Connolly still offers as an attacking force.
And Whittingham believes this veteran, in the twilight of his playing shelf life, can spring a few shocks.
The Blues boss said: ‘I think David will be a surprise to a lot of League Two teams over what his ability is like.
‘He undoubtedly still has the ability to play higher up the leagues.
‘David has got the attitude that he wants to succeed, the determination to succeed and also he is a pest.
‘He will keep working, keep going, keep trying to find space, keep trying to do things with the ball, keep making runs, so centre halves won’t be allowed to switch off for a second.
‘Those League Two defenders will find that out for themselves this season.
‘I am not going to put any pressure on him by setting targets, the good thing is we have got a front four now competing for places up front and it spurs them along.
‘We all appreciate David as a footballer because everybody sees him on the football pitch and the attitude towards the game when he is playing.
‘What we see more is the attitude off the pitch that other people don’t. He’s first-class and is a top pro.
‘David wants everything to be done right, even though we haven’t got the facilities or the ability to do everything top notch.
‘He still believes, as we do, you do things to the best of your ability all the time.’
Last season, Connolly netted seven goals in 17 appearances after joining the Blues in January.
His outstanding impact was largely unexpected after a spell out of the game after leaving Southampton in January.
Yet the former Republic of Ireland international demonstrated energy levels and enthusiasm which defied his age.
Whittingham believes Connolly also brings the best out of his team-mates.
He added: ‘The other players here realise they have got somebody who is going to make sure he drags them up to his standard.
‘I am not saying none of them are at that level.
‘But it’s great to learn from someone as experienced as David.
‘He still wants the best and the younger players can see that.
‘It rubbed off on them a bit last year and I am sure it will again this year.
‘He is demanding as far as he wants things done well, which is great because it keeps everybody on their toes – even the staff!
‘That’s what it is all about, you don’t know everything and there are things you might class as not important as others so concentrate on something.
‘Then David comes along and says “that isn’t right” and he has a point – so we change things.’