From locking horns with Tonbridge Angels and Heybridge Swifts to facing Sheffield United at Fratton Park.
Yassin Moutaouakil’s once-promising career is back on an upward curve after recent troughs.
And Guy Whittingham is convinced the rejuvenated right-back can continue to blossom in his Pompey surroundings.
The 26-year-old penned a one-year deal with an option to extending it on Thursday, becoming the latest player to commit to the Blues.
It marked a turnaround in the career of the former France under-21 skipper who spent half of last season with Hayes & Yeading in the Blue Square Bet South.
Steve Allen, who knew Moutaouakil from their Charlton days, brought him to Pompey initially on trial – and Whittingham snapped him up.
In total, he has made 19 appearances for Pompey and Whittingham is confident Moutaouakil will keep shining.
He said: ‘I have been very impressed with Yassin since he joined us. I think he has improved as he’s got back into full-time football again.
‘Towards the end of the season there weren’t many left-wingers getting past him and people have seen as well he likes to get forward, so as a right-back in this league we are very pleased.
‘I think he is very similar to Therry Racon, in terms of having been out of full-time football for a while, but I was very encouraged by the way he played his last half-a-dozen to 10 games for us.
‘We all know there are a lot of teams that just get the ball into the box, but when I have gone three at the back at times, he has gone as one of the three.
‘So I don’t think he is worried about aerial challenges. He is a big enough guy that can cope with it and a strong enough player that can do that as well.
‘It is very important we have full-backs that can push on but also understand being organised at the same time and how much to push on and how much not to.
‘I think that was what he was getting towards the end of the season, his timing at making the runs was good.
‘He got a bit frustrated he wasn’t used enough attacking-wise but we were more than pleased with the way he defended.’
Pompey had been keen to tie Moutaouakil to the club on a two-year deal, as they have with other new signings.
But it was the Frenchman himself who pushed for 12 months, although there remains an option to extend that.
Regardless, he is in pole position to be first-choice right-back once again next season.
Although, Whittingham has warned there is no such guarantee in place for the well-travelled former Motherwell player.
And with more signings on the way he may face a scrap for his spot.
‘We wanted Yassin longer but he wanted a year,’ added Whittingham.
‘That is up to him. We are happy he is here for a year and within that year we hope he has a good enough season and he wants to stay again.
‘I am not going to say he will be the regular right-back because he will have to play well, but we are getting players in where there is competition for places all over.
‘If he plays like he did at the end of last season then he will be our regular right-back.
‘If he doesn’t, then, like most teams, you will play the best players you think are doing well.’