But the long-serving left-back admitted it still proved a 'bitter-sweet' occasion knowing it could be the last time he features for the club where he's spent more than 20 years.
Bailey, 29, first featured for Moneys as an eight-year-old in the youth ranks and made his debut for the first team at just 16 in April 2009.
Now, as he heads for a new challenge at AFC Portchester, he stands as the club's record appearance holder, featuring an incredible 424 times over the course of the past 12 years.
The Southsea lad's last Moneys appearance - at least for now - came in their penalties victory over Baffins Milton Rovers at Fratton Park last Thursday to win the delayed 2019-20 season Portsmouth Senior Cup.
It was a befitting occasion for Bailey to say his final goodbyes to a club he has served so honourably - although it still didn't make things any easier for him.
He said: 'It was the perfect way to go out. I really wanted to win the trophy, obviously, but it’s a bit of mixed emotions where I made my first team appearance when I was 16.
‘I joined when I was eight - I’ve just been there ever since.
‘It’s a bit sad to leave, I’ve had some great memories.
'It’s a tough one to leave. They’ve got some great people off the field who do a lot of work that goes unnoticed and I’ve made some great friendships there.
‘If I didn’t leave now I don’t think I ever would. I might look back and regret it, but it’s a chance I wanted to take. Portchester look like a club who want to go in the right direction.
’It’s bitter-sweet to leave. I do look back with a lot of pride. I think my dad, he goes and watches every game home and away, he’s quite proud. There are a few of the locals over there and it was hard to say your goodbyes to them.
‘I’ll still go over there and watch them when I haven’t got a game and cheer them on - I wish them all the best.'
After rising through the club's youth ranks, former manager Miles Rutherford handed Bailey his debut in a 2-1 Wessex League Premier Division defeat at Bemerton Heath Harlequins on the last day of the 2008-09 season. It was a first appearance to remember, as Bailey came off the bench to score Moneys’ consolation goal.
It didn't take long for the left-sided youngster to make an impression, as he netted in his first appearance after coming off the bench.
Since then, a further 423 appearances and 40 more goals have followed. Bailey has enjoyed his share of success on the pitch with Moneys, twice winning the Portsmouth Senior Cup, along with Russell Cotes Cup glory and promotion into the Southern League for the first time in the club's history in 2017.
But it's getting the chance to play in the FA Cup, FA Vase and FA Trophy that have filled him with most pride during more than a decade as a senior player at Dover Road.
Bailey said: 'I scored that day (on my debut) - I think it was the 100th goal of the season as well!
‘I was a left midfielder when I was younger but when I got slower then I went to left-back.
‘It’s probably just like the cup runs in the FA Vase and the FA Trophy (highlights) - for non-league players they’re massive. The buzz you get from playing in them, especially if you go through a few rounds, they’re the memories that stick out for me.
'We went to the play-offs in the Southern League and got knocked out by Yate Town (in 2018/19) - that was a good game and one I enjoyed.'
But now is the time to focus on new beginnings for Bailey after a remarkable Moneyfields association.
He has opted to follow former boss Dave Carter and a number of fellow Moneys men in joining AFC Portchester for next season.
Bailey won't have long to wait for a return to Dover Road as a player, with Moneyfields dropping back down to the Wessex League Premier after taking voluntary relegation from the Southern League.
Bailey joked he'll probably walk into the home dressing room on his return.
But, on a serious note, he hopes making the switch proves the correct decision with ambitious Portchester targeting promotion to the Southern League for the first time in their history.
Bailey, who was asked to stay on at Dover Road by incoming boss Glenn Turnbull, said: 'It was a really tough decision (to leave Moneys). I may regret it, I may not, but I can’t dwell on it now.
‘Portchester is a good club, I’ve been over and had a look, they want to do things the right way so it’s exciting and I’m looking forward to it.
‘It’ll be weird that will (returning to Moneyfields) - I’ll probably walk into the home changing room!
‘Personally, my time at Moneyfields has been brilliant. Everyone there, every manager and every player, I haven’t got a bad word to say about anyone.
‘I’d do it all over again.'