Attending the 2008 FA Cup final at Wembley with his grandparents then cemented a love affair that will be put to the test today when Huddersfield Town look to avoid becoming one of those upsets.
Holmes-Dennis is expected to make a rare start against League One Rochdale and, while Spotland on a freezing January afternoon is perhaps as far removed from Wembley on Cup final day as possible, he can already feel the tingle that accompanies a tie in the world’s oldest knockout competition.
“The boss loves the FA Cup,” said the 21-year-old ahead of the fourth round clash. “We all do. It is a great competition, the best in the UK. And the further you go, the bigger it becomes.
“I am not sure if the German lads know all about the FA Cup but all the English players do. When they see how buzzing we are for it, I am sure they will be the same.”
Holmes-Dennis joined Huddersfield in the summer from Charlton Athletic and has since made five starts. The exceptional form of first choice left back Chris Lowe accounts for such a meagre tally.
Nevertheless, Holmes-Dennis has shown clear signs of progress under the tutelage of David Wagner and today he is hoping to put in a similarly impressive performance as the one that helped Huddersfield cruise past Port Vale in the third round.
“The FA Cup is really special,” added the Farnborough-born full-back. “I was lucky enough to go to the final when Portsmouth won it.
“My grandad and grandma took me. I was quite young at the time but it has stuck in my mind. The experience was brilliant, a great day out and the atmosphere was unbelievable.
“I also went to the Championship play-off final between Watford and Crystal Palace (in 2013). That was the same sort of atmosphere.
“But I have always liked the FA Cup as it is that little bit different. When young, I enjoyed seeing the bigger teams beaten by the little teams. Now, though, I want to beat Rochdale. I haven’t played there before but I am looking forward to it
“Our attitude will be vital. We must approach the Cup tie like we do all games and not be complacent. If we do that, we give ourselves the best opportunity of going through.
“Rochdale will have seen how well we have been doing in the league and will want to beat us. It might be like their Cup final so they will be putting their heart and soul into it.
“That is why we have to approach it in the best manner. But, hopefully, we can go into it with the same attitude and then our qualities will show.”
Around 3,500 fans will be following the Terriers on the short trip to Rochdale for a tie that pits against each other two teams currently occupying a play-offs berth in their respective divisions.
Dale, conquerors of Leeds United in the Cup not so long ago, have already seen off Maidstone, Barrow and Carlisle United to reach the fourth round
Town, meanwhile, made light work of dismissing Vale 4-0 in the last round – the Yorkshire club’s first win in either the League or FA Cup since 2014.
Further progress today will provide Wagner’s side with the opportunity to land either a plum tie in the fifth round or, failing that, a fighting chance of going even further and booking a place in the quarter-finals for the first time since 1972.
For Holmes-Dennis, an extended run in the Cup would help cap a move that he has really started to relish after admitting to suffering from a bit of homesickness early on.
“At first, it was a bit difficult due to being away from my family,” added the left-back, who earlier in his career had loan spells at Oxford United, Plymouth Argyle and Oldham Athletic. “But now I enjoy being up here. All the lads have been great. Playing with (captain) Mark Hudson is great, his experience and advice is second to none. You can’t have too much of that.
“It is the same with Jonathan Hogg in midfield and Dean Whitehead. People like that have been playing for years and their advice is a big help. I also spend time away from the club with quite a few lads and that has been a big help.”
Asked if Sean Scannell, who made the same trip from south London to Huddersfield in 2012, had been a big help in settling, Holmes-Dennis laughs before replying: “Scanz is not a London boy any more.
“He is a Yorkshire boy now. I am doing the same, adopting the lifestyle up here. It is less hectic compared to London. I enjoy it.
“All the lads have been great. It is a club where everyone helps each other out. People like ‘Scanz’ have been here forever.
“And then there are quite a few like me who have only been here six months.
“There are a few of us - Kasey (Palmer), ‘Scanz’, Jack Payne, Nahki (Wells) - we all go out for food. It is good to have friends around you as it means you settle.”
Along with finding his feet in the area, Holmes-Dennis has also had to adapt to the demands of Wagner and his gegenpressing system. Again, the sounds are good.
“I feel comfortable with the team and have been learning the way we play,” he said. “Every game, I feel more confident. Ideally, you want to accumulate a run of games but I have to just take each opportunity as it comes along.”