It is the same club where he first learned to play rugby as a four year old, the place where friendships were formed, his love for the game developed and the foundations were laid for a career that would eventually take him into the Energia All-Ireland League and representative rugby.
There have been plenty of memorable experiences along the way. But few will carry quite the same personal significance as captaining his hometown club into their first ever home fixture in the Energia All-Ireland Men's Junior Cup.
At 2.30pm on Saturday, Clonakilty will welcome Ulster side Dromore to West Cork for a quarter-final that represents another important chapter in the club's history. For the 29 year old captain, it is an occasion that brings his rugby journey full circle.
From the youngster who first pulled on a Clonakilty jersey more than two decades ago to the experienced player now entrusted with leading the senior team, Jennings understands what moments like this mean to a club and its community.
“Firstly it's a massive honour for me to be representing my home club” Jennings told irishrugby.ie.
“It's where I learned my bread and butter. I started off there when I was about four years of age. I had a spell away when I went to college and was working in Cork before this.
And I came back maybe, I think this is my fourth year back now, and I captained the club last year and we had a fairly successful year and we're reaping the rewards of it now, like going into the quarter-final this weekend.”
Clonakilty's involvement in the national competition is significant in itself.
The West Cork club previously competed in the All-Ireland League, but it has been approximately 13 years since they were relegated. Clonakilty suffered a 26-23 defeat to Richmond, a sad day for the club as their twelve years as a senior club came to an end before a very large crowd at the West Cork venue.
That Division 2B encounter was the last time their senior side last experienced a national occasion of this magnitude on home soil.
Now, having earned their place in the Junior Cup, they have an opportunity to bring that excitement back to The Vale.
“I suppose it's a massive occasion” Jennings said.
“It's the first time Clonakilty have ever hosted a game of this kind of magnitude, really, since we were in the All-Ireland League 13 years ago now. So yeah, it's a massively proud moment for me and my family.”
The journey that has brought Jennings to this point has taken him well beyond West Cork.
After progressing through Clonakilty's underage ranks, he attended Bandon Grammar School before moving on to University College Cork.
His rugby development included college rugby, representing Munster at U19 level, while he also gained experience with Munster A on their trip to Boston for the 2019 Cara Cup, alongside a spell playing Energia All-Ireland League rugby with Dolphin.
Jennings has also lined out for the Munster Juniors in their recent interprovincial series too. Those experiences allowed him to test himself at different levels of the game, develop his understanding of rugby and play alongside talented teammates.
But eventually, the pull of home became difficult to ignore.
Away from the pitch, Jennings is immersed in the agricultural life of West Cork.
He farms dairy cattle at home and works with local company Deane Dairy Equipment, fitting and servicing milking machines.
Whether he is working on the family farm or travelling to service equipment, cows are rarely far from his daily routine.
That lifestyle made the demands of commuting for rugby to Virgin Media Park increasingly difficult to justify.
And when the opportunity arose to return to Clonakilty, the decision felt like a natural one.
“I suppose the biggest change was the relief of not having the commute” he explained.
“Living in Clonakilty and farming in Clonakilty, it made more sense for me at the time to move back to my home club. It was a couple of years in the making.
“In my own head, I'd say I'd been there, done that with my AIL, and I'd experienced it, and don't get me wrong, I enjoyed it thoroughly.
But it was nice to come back to the home club and give back a bit again because they were so good to me growing up, do you know what I mean.”
That desire to give something back has become an important part of Jennings connection with Clonakilty.
He has experienced rugby at a higher level and represented his province, but the relationships and sense of belonging he has found at his hometown club remain difficult to replicate.
It is something he values even more now that he captains the club.
For Jennings, leadership is not simply about delivering speeches before important matches or making decisions on the field.
It is about representing a group of people who have become an important part of his life.
“It's hard to explain, the group of lads we have there, they're a great bunch of lads and they'd do anything for you” he said.
“Anyone in the management side of it and the player side of it, if you have a problem, talk to them, they'll sort it the best they can, and the lads have your back. So no, it is definitely the best I've probably played with in all of my rugby career.”
That togetherness has helped Clonakilty develop into a side capable of competing on the national Junior Cup stage.
Their debut in the competition could hardly have gone much better.
Drawn away to Ballina in the opening round, a side with recent history of playing in the AIL, the Cork side travelled to Mayo and produced an impressive attacking display to secure a 48-14 victory.
Ben Lovell enjoyed a particularly memorable afternoon, crossing for a hat-trick as Clonakilty announced their arrival in emphatic fashion.
For a squad experiencing the competition for the first time, the result provided both encouragement and the reward of a home quarter-final.
“I suppose it's our first time in it, so we're finding our way at the moment” Jennings said.
“We had a nice win away in Ballina to put us in this position, to give us the opportunity to have a home game of this magnitude.
And the lads are up for it, they're excited, and they can't wait to hit the ground running on Saturday lunchtime.”
The victory in Ballina was particularly satisfying because of the momentum Clonakilty established once they settled into the contest.
Jennings acknowledges that some moments went their way, but believes the team's work rate and attacking confidence were central to the performance.
“I suppose we got the rub of the green there when we were above there” he reflected.
“But we worked hard to get going, and when we got going it was kind of hard to stop the momentum from us I suppose. So the big focus for us this weekend now is to keep the head down and get going, start as well as we did up there, and keep the momentum rolling. And hopefully put on a performance for the home crowd and take it to the semi-final.”
That ambition will face a considerable examination against Dromore.
The Ulster club have developed a strong reputation in Junior rugby and arrive in West Cork regarded as one of the favourites to challenge for this season's competition, having made it to the final last term.
Their experience at this level provides an additional obstacle for Clonakilty, who are still discovering what it takes to compete in a national knockout tournament.
But Jennings believes the underdog tag can be a source of motivation rather than intimidation.
“They've been in it a couple of years now and they're looking like the favourites for the weekend” he said.
“But going into a game as an underdog kind of gives you a bit of a chip on your shoulder and makes you work that small bit harder.”
That attitude has been evident in Clonakilty's preparations.
Following a demanding weekend in the Munster Junior League, Jennings has been encouraged by the response from his teammates at training.
“The lads put down a great training session on Wednesday night” he explained.
“And no doubt the captain's run on Friday, it will be short, sharp and precise. Everything will be nailed down and we'll know what to do on Saturday, come kick-off.”
Clonakilty's approach to the fixture is built around a determination to concentrate on their own performance rather than become overly concerned with the opposition.
Jennings knows Dromore will bring quality and physicality to the Vale, but believes his side must remain confident in the rugby that has brought them this far.
“What we do at training is we focus more on our own stuff” he said.
“We don't try to dwell on the opposition that we're playing.
Obviously the coaches will tailor our session plan to what we need to work on, what needs to be better and what will be effective at the weekend coming.
But we generally don't dwell on other teams.”
That does not mean Clonakilty are underestimating their visitors.
The coaching staff have been studying Dromore and preparing the players for the challenges they are likely to face.
But Jennings prefers a straightforward approach.
“We don't look at them as threats really, in terms of, oh, they have two or three great big players, they're going to run the ball down” he explained.
“It's rugby at the end of the day, it's a fairly simple sport.
It's a contact sport, take down your opposite man and that's it, score more points. I suppose we wouldn't dwell on it, the whole looking into it too much, but no doubt the coaches have seen video footage and they've been tailoring our plans.”
There is a refreshing simplicity to that message.
Clonakilty know the importance of the occasion, understand the quality of their opponents and recognise the opportunity to reach a national semi-final.
But once the match begins, the fundamentals of rugby will remain the same.
Jennings wants his teammates to trust their preparation, embrace the physical contest and produce a performance that reflects their capabilities.
“Well the main thing is putting in a performance and hopefully with that comes the win” he said.
“But I back the lads. As I said, we had a sharp training session there on Wednesday night and we know our stuff and we know what our plan is for the weekend.
And we're going to get going and get it going.”
That confidence has been particularly important following last weekend's disappointment in the Munster Junior League.
Clonakilty suffered a 21-3 defeat against local rivals Bandon, a result that interrupted their momentum and provided a reminder of the challenges involved in maintaining consistency.
The rivalry between the neighbouring West Cork clubs is a fiercely contested one, with matches often decided by physicality, determination and small margins.
Clonakilty had beaten Bandon earlier in the season, but were unable to repeat that success in their latest meeting.
Jennings makes no attempt to disguise the disappointment.
“Last week was a tough one” he admitted.
“The local derby games are always big bruising physical games and there's no love lost between ourselves and Bandon.
We always have a good cut at each other. Look, we beat them at the start of the season, but we fell short last weekend.”
Yet the timing of the Junior Cup quarter-final offers an immediate opportunity to respond.
Rather than dwelling on the derby defeat, Jennings wants Clonakilty to channel that frustration into a determined performance against Dromore.
“100% we'll be looking to face into this weekend now and a bit of a response from the lads” he said.
“We've kind of seen that in training on Wednesday night, that the lads are keen to get a good response at the weekend against Dromore.”
For Jennings, the challenge is about more than securing a place in the semi-finals.
It is about giving the club and its supporters an occasion to remember.
The Vale has been part of his life since he was a small child, and he knows how much the club means to the families, volunteers and former players who have helped sustain it over the years.
Many of those people will be watching on Saturday afternoon, hoping to see Clonakilty take another significant step forward.
The captain wants his teammates to appreciate the moment.
“We all know how to play rugby, we've all played rugby long enough. These days don't come around very often, so go out there, enjoy it, perform to the best of your ability, leave no stone unturned.
“And I don't doubt the lads, I don't doubt them about that. If we put 110% effort into it, it'll be there for us, all going well.”
That message reflects his own experience of rugby.
Jennings has played in the Energia All-Ireland League, represented Munster at different levels and travelled overseas with Munster A.
But he understands that occasions such as Saturday's quarter-final can carry a significance that goes beyond the standard of competition.
There is something different about representing the club where it all began.
Something different about looking towards the touchline and recognising the people who helped shape your rugby journey.
And something particularly meaningful about knowing that younger players are watching, perhaps imagining themselves one day wearing the same jersey.
For Clonakilty, the Junior Cup run offers an opportunity to inspire the next generation.
Jennings remembers what it was like to be a young rugby player, eager to watch the senior team and dreaming of following in their footsteps. Watching a team that was playing in a competition like the All-Ireland League.
Now he finds himself on the other side of that relationship.
“As a young fella, sure you can't get enough of rugby” he said.
“So young fellas to be standing out on the side of the pitch, and girls, the women's team are going well as well.
So to have young boys and girls out there watching and supporting us there, it's massive.”
That connection between the senior team and the club's underage players is already an important feature of matchdays at The Vale.
Youngsters regularly gather to welcome the players onto the field, creating an atmosphere that reminds the senior squad of the wider community they represent.
“During the regular season with Junior League, we'd have the youngsters, they'd be out clapping us onto the pitch and everything like that” Jennings explained.
So it's massive. It kind of makes you feel like a superstar and it kind of gives you that extra oomph to put on a performance and to give them a show. So it's a massive occasion for us.”
It is easy to imagine the excitement those young supporters will feel on Saturday.
For many, this will be their first experience of watching Clonakilty compete in a national knockout fixture at home.
The possibility of reaching an All-Ireland semi-final adds another dimension, but the occasion itself already represents a significant achievement.
Clonakilty have a proud rugby history, including their years competing in the All-Ireland League and as a senior club in Munster.
Those memories remain important to the club, but Jennings and his teammates now have an opportunity to create something new.
A victory over Dromore would take them into the last four of the Energia All-Ireland Men's Junior Cup and provide further evidence of the progress being made in West Cork.
It would also reward the players, coaches and volunteers who have helped the club reach this stage.
But Jennings is reluctant to become distracted by what might happen beyond Saturday.
His focus is on ensuring Clonakilty approach the game with confidence and give everything they have.
The result, he believes, will follow from the performance.
“If we go into Saturday with our heads down, sure we know what's going to come” he said.
“So we've just got to go in, head held high, give it everything and let the result take care of itself.”
It is a fitting message from a captain whose rugby career has brought him back to the place where it started.
From the four year old learning the game at Clonakilty, to the schoolboy at Bandon Grammar, the UCC student, the Munster representative and the Energia AIL player with Dolphin, Jennings has experienced plenty along the way.
Away from rugby, his days are filled with dairy farming and working with milking equipment across the West Cork area and beyond.
But when Saturday arrives, those responsibilities will give way to something that has been part of his life for more than two decades.
Pulling on the Clonakilty jersey.
Leading his teammates onto the pitch.
Representing the club that gave him his first opportunity to play rugby.
And perhaps most importantly, helping create the kind of memories that inspired him as a youngster.
Dromore will arrive with experience, quality and the expectations that accompany being regarded as one of the competition's leading contenders.
Clonakilty will have the advantage of familiar surroundings, a passionate home crowd and a squad determined to respond to last weekend's disappointment.
The stakes are considerable, with a place in the national semi-finals awaiting the winners.
But for Jennings, there is another reward already within reach.
The opportunity to look around The Vale, see the next generation of Clonakilty players watching from the sidelines and know that his hometown club is once again enjoying a significant occasion on the national stage, and to banish the memories of that April afternoon in 2013.
It is the kind of day that does not come around very often.
And after returning home to give something back to the club that helped shape him, Dave Jennings is determined to make the most of every moment.