Holmes Park provided a glimpse at the present – and potentially a glance at Pompey’s future.
The base of the Leicestershire & Rutland County Football Association served as Monday evening’s stage.
Among those in attendance at the under-23 encounter between Leicester City and Chelsea was Phil Boardman, the Blues’ head of recruitment.
‘Long-term planning involves making sure you are aware of players who might not necessarily be ready for loan in January,’ said the former Wolves head of performance analysis.
‘But come the summer or following January, these players are 6-12 months older and perhaps ready. We are tracking ones we may go for in the future.
‘For all the players we bring in, there are a hell of a lot of others we’re watching and have been doing a lot of work on. They could end up in a Portsmouth shirt in the near future, you never know, these things can change quickly.
‘There may be a player we are watching now that in 18-months time we shall move for.’
The outcome of that night in Whetstone was a 2-1 success for the Foxes, Callum Wright and Tyrese Shade the scorers, duly noted by Boardman, no doubt.
Having been appointed to the role in September 2017, next month marks his third transfer window.
Last summer, of course, represented an outstanding period of recruitment, the vast majority of the six permanent signings arriving within five weeks of the season’s end.
And leading the way was Ronan Curtis for a bargain £100,000 from Derry City.
‘Ronan is an example of all parts of the club coming together to hopefully find a player who is going to improve the squad and improve the team,’ added Boardman.
‘Initially it was part of our scouting network, identifying the player, following up on those initial observations, a lot of video work and speaking to contacts in Ireland.
‘We feel we have some decent contacts over there who watch that league fairly regularly and give us that additional information.
‘As the case with a lot of the players we have suggested, it’s my job to coordinate all the information and see where I best go and watch the player for the next set of observations.
‘There were several trips over to Ireland and to watch a wider range of situations so we get an idea of what he might play like at home or away, for example.
‘Ronan has a really good attitude and work ethic about him that endears himself to what Kenny wants. The Portsmouth fans also like to see players play with a lot of heart and a lot of attitude.
‘He has an eye for goal from wide and we had a gap in the squad for that position. We are looking for goals from around the pitch to help the forward.
‘Brett Pitman did really well last year, but our goals were quite heavily focused on one player, so spreading them around and contributing goals and assists from wide is something which was going to attract our interest.
‘It was fairly well publicised quite a long way out from the transfer window that there was some interest from ourselves. Then there was a little bit of toing and froing with Derry and the agent – and Mark Catlin and Tony Brown did really well to get the transfer over the line.’
Anton Walkes was another purchase, while Craig MacGillivray, Tom Naylor, Lee Brown and Louis Dennis arrived on free transfers.
And their paths to Fratton Park were diligently plotted long before the summer window opened for business.
Boardman said: ‘MacGillivray had an excellent performance against Portsmouth for Shrewsbury - and there is no better way to catch the manager's eye than playing against his team at Fratton Park.
‘He featured fairly regularly in the Checkatrade Trophy on their way to the final, so we were able to watch several of his games during that competition.
‘Last season he had a young loan keeper from Manchester United ahead of him and his chances were relatively limited, but the games we saw he performed very well in.
‘Dean Henderson is an excellent goalkeeper and in the Championship this year with Sheffield United, so the fact Craig was number two doesn’t necessarily mean he wasn’t ready to step up and be number one at Portsmouth.
‘With Lee Brown, we work windows ahead and fundamentally have to know our own league as best as possible. We were aware of his contract situation.
‘While we are looking to branch out in our knowledge of players in different areas, yet must still focus on our own league and have an in-depth knowledge of players’ circumstances. We speak to agents and other people in the game to get that information.
‘Tom Naylor is someone we knew quite well from watching Championship games over the years.
‘We felt that position would benefit from bringing in a little bit of experience, a slightly older player who has performed higher and knows what it is to get out of League One.
‘It was felt Tom was one who could help us get promoted this season. He has Championship experience, leadership, knowledge of how to get out of this league - and there was a contractual situation we were aware of.
‘We worked over a long time to convince Tom that Portsmouth was the right club.’
Of those summer recruits, to date MacGillivray and Brown have been League One ever-presents, while Naylor and Curtis have missed two league matches apiece.
The quartet have been pivotal presences in a team which has topped the table for approaching two-and-a-half months.
Boardman added: ‘It’s good to see the team doing well, but we won’t be resting on our laurels on what we have achieved so far.
‘We must regard last summer as having the right effect on the team – and use that as a blueprint to continue our work moving forward.
‘The proof, I suppose, is in the performances, but recruitment is not a hard and fast rule. The ones that have come in so far have fitted in well, hopefully that continues.’