Weymouth host Dorking Wanderers in the National South play-off semi-final on Saturday - led by manager and former Cherries player Mark Molesley.
With that in mind, we caught up with the Terras' boss - who also continues to work at AFC Bournemouth as assistant to Shaun Cooper with the under-21s - and talked about Molelsey's time with the Cherries.
A veteran of the club's Greatest Escape of 2008/09, Molesley will go down in history as Eddie Howe’s first signing in management.
The tenacious midfielder had diligently plied his trade in non-league before he joined the club permanently – aged 27 – in January 2009 following a loan spell.
Molesley went on to star as Howe led the Cherries to their memorable escape from relegation, only for a series of injuries to check his progress as the club climbed through the leagues.
He finished his playing career with spells at Aldershot and Weymouth before returning to Vitality Stadium to join the club’s coaching staff in August 2015.
How did your move to AFC Bournemouth come about?
I was training with Grays Athletic in the Conference at the time and they had hit some financial difficulties and couldn’t pay the players.
The news must have got out because Grays had a phone call from Bournemouth asking if I would be available to come here on loan.
At 27, I’d been in non-league all my career so it was a dream come true. Even if I only stepped foot on the pitch for a minute, at least I could say I’d lived my dream of being a proper professional and played in the Football League. It was a chance I jumped at.
To go on loan, I had to terminate my contract with Grays so I was putting all my eggs in one basket. I wouldn’t saying I had nothing to lose because I had everything to lose.
The loan was until New Year’s Day and, if it hadn’t gone well, I would have been without a club and a contract. I thought you only live once and this had always been my dream.
You made an inauspicious start and must have wondered what you had let yourself in for?
It was an eye-opener. I remember walking into the changing room at Shrewsbury and seeing Darren Anderton and Lee Bradbury, two players I had watched on telly. I thought “haven’t I done well to be sitting in this changing room”.
Results didn’t go too well. One of my first games was at Accrington and we were booed off after losing 3-0 and rightly so.
I remember thinking it wasn’t the greatest start but I had everything to prove and had to make it work. I was relishing and enjoying the challenge.
The club was fighting for its life and so was I. I’d taken a gamble to come here so had everything to fight for and was willing to give it everything I had. It was bittersweet. I was gutted about results but was also getting an opportunity and knew I had to take it with both hands.
Can you recall the events of New Year’s Eve 2008 and New Year’s Day 2009?
I was gone. I’d got my shirts from the kitman and was driving back home to London, wondering where it had all gone wrong. I thought I’d done quite well and had had some good games.
I didn’t have an agent but nobody had said anything to me. In the end, I bit the bullet and went to see the manager (Jimmy Quinn) a few days before New Year’s Eve. I said my loan was finishing soon and asked if I was going to be offered anything. He said nobody had spoken to him so his advice would be to find another club. That gave me a sinking feeling and I was gutted because it was over.
My league dream had spat me back out and I was really dejected. Then, I had a call from someone at the club telling me not to sign for anybody. They said all would become apparent in the next few hours. I hoped it would be a lifeline.
I was at a New Year’s Eve party at my uncle’s and the gaffer (Eddie Howe) phoned me. He said he wanted me to come back tomorrow. I had to duck out of my uncle’s basement to take the call and I think the gaffer has always thought of me as some sort of party animal.
The next morning, I drove back to Bournemouth and signed until the end of the season. What an amazing 24 hours it was. I went from the bubble bursting and in despair to getting another crack at it.
What are your memories of the second half of 2008/09?
It was the best time of my playing career. And apart from getting married and having children, it was the best part of my life. I look back with fond memories. As a group, we had a very strong bond.
It was great to see the Minus 17 documentary because it captured everything so perfectly. I don’t think some people realised quite how it was at the time.
It was backs against the wall and us against the world. When you achieve your goal, there’s no greater feeling and we certainly achieved something that season. It will live long in my memory.
The next three seasons, however, did not go as you would have wanted?
The following season, we won nine of our first ten league games, were top of the table and I’d had a few man-of-the-match awards. I felt like I’d arrived.
My wife had moved down and she was pregnant with our little girl. Life could not have been better. It was everything I had ever dreamed of and wanted.
Then, I was jogging in training one day and felt my foot. My ankle locked and I thought it didn’t feel right. I thought if I kept running, it was sort itself out so I finished the session.
I played the next day against Accrington with painkillers. We were flying and so was I and I didn’t want anything to stop the momentum.
But I played the next game and had to come off in the second half. I couldn’t walk or put any weight on my foot.
I had X-rays and my navicular had a lot of stress fractures and looked a mess. I went into a boot and hoped it would heal in six to eight weeks.
But I came back and trained and there was no change. I couldn’t run or bend it. I went under the knife and the operation robbed me of the whole season.
It was a painstaking rehab process and it felt even worse after I had gone for my first run. That was a tough time and brought me to my knees. After I had broken down, I thought my career was over because they said I might not play again.
I found another surgeon who thought he could save me and get me back playing. I had really intrusive surgery and was out for the best part of 18 months.
I got back training and playing but kept having other injuries. Every time I played, I was in pain. It was tough.
I remember coming on against Oldham in March 2011 after being out for 18 months. The crowd chanted my name and the reception I received made it all worth it.
Ultimately, I got back but, unfortunately, a succession of injuries after that took their toll and then I developed tendonitis in both Achilles.
Unfortunately for me, the gaffer then moved on and, although I got myself playing, a lot of new signings had come in and we had a new manager. I didn’t get a look-in and trained with the under-21s. It was difficult.
Eddie Howe’s return to the club in October 2012 gave you a massive boost?
He brought me straight back into the fold. He asked me what I wanted to do and I said I wanted to get a month of games under my belt. I went on loan to Plymouth and had my first run of games in two years. But I strained my hamstring and had to come back.
By then, the gaffer had taken the club to a new level and the last thing I wanted was to be a burden. I knew I was going to struggle to get games with players like Shaun MacDonald, Eunan O’Kane and Harry Arter in the squad. I wanted to play and he let me leave.
How key a role did Eddie Howe play in your career?
I’ll always be grateful for being his first signing and for the way he picked me up when he came back.
He probably doesn’t even realise or remember but just the way he spoke to me the first day, I felt like someone had some respect for me.
I had the best time ever playing for this club. I came here when I was 27 and was told I’d never play again at 28. But I continued until I was 35 and will always be grateful for every game I played.
This feature first appeared in the Watford edition of MATCHDAY, the club's programme, earlier in the 2019/20 season.