It was an evening where past, present and future collided. A game where Gosport Borough manager Alex Pike truly began the process of building a squad for the future.
Nineteen players were given an opportunity to impress on a warm summers evening, better suited to cricket and most took their chance to impress. From that point of view, if Boro' can build on the positives that appeared in Hampshire's capital city this evening then there can be some justifiable optimism about the approaching season.
However he was also briefly haunted by his past as former Boro' striker and fan favourite, Ollie Bailey scored twice for Craig Anstey's Citizens who won the game 3-2. Winchester's squad also included other former charges such as goalkeeper Ryan Price and midfielder Jamie Barron.
But Pike was only thinking of the future. In his starting eleven, only Aaron Dawson, Declan McCarthy and Ellis Grant (pictured) remained from last year's Senior Squad.
In the second half, Lewis Watch replaced Grant in goal and the remainder of the squad was comprised of the new arrivals that will form the bedrock of the future Gosport team. These included Matt Buse, Alek Przespolewski and many more.
Sitting his players down in front of the dug out at the City Ground at the final whistle,Pike praised them for many fine individual performances and never-say-die attitude.
This, they certainly had in spades. Jack White headed the home side in front early on before Bailey made it two in an impressive display from the diminutive striker who only left Privett Park a month ago.
Then, with Winchester having looked the sharper, Boro' got a foothold in the game. Chilton Vine's shot on the turn left Pryce with no chance and his goal left the half time score at 2-1.
Cue wholesale changes for the second half. Bailey made it three with an impressive shot on the turn which sailed high past Watch into the roof of the net but Gosport soon reduced the arrears once more with a fine individual strike from Liam Kimber whose doggedness was rewarded with the space and time being created to allow him to fire a diagonal shot past Pryce.
The post match debrief by Pike, his assistant Danny Thompson and coach Steve Stone was positive.
Gosport now move into a week of intense training before their next outing against Bemerton Heath in Wiltshire, a week on Thursday (20th July).
As far as an opening friendly for a new look squad after just one week of training goes, this was a decent effort. The Management will be looking to take this one step further with the Southern Premier League season just five weeks away.
Updated 16:39 - 8 Jul 2017 by Site Manager