The Magpies' lead under-18 coach is a former Newcastle youth team player who twice represented his boyhood club in the competition in the early 1990s, and the UEFA Pro Licence holder is now helping to develop the likes of Elliot Anderson and Joe White at the club's Little Benton Academy.
Highly-rated Anderson - who has twice been an unused substitute for Steve Bruce's first team this season - will feature for United's youngsters against the Terriers in the third round clash, while England under-18 international White and prospects including Lucas de Bolle and Nathan Carlyon will also hope to shine in a game which is being shown live on the home club's official YouTube channel.
And Winskill, who replaced Dave Watson as under-18s coach in the summer of 2019, told nufc.co.uk: "I think the tradition of the competition means that it's one of the fixtures that everybody looks out for when the schedule comes out at the beginning of the season.
"People look at when the local derbies are, and then when's the Youth Cup? It's a long-standing competition, it's got a lot of history attached to it and it means a lot to the players. It's something they all look forward to.
"We always say that it's about providing them with opportunities to learn and get experiences that will stand them in good stead for the rest of their football career, so playing at a stadium, under lights - in normal circumstances, with a crowd - and it's a knockout competition. We always play to win, while playing our way, and never more so than tonight, the prestigious competition that we're in."
Unfortunately, Huddersfield's 24,500-capacity stadium will be virtually empty due to Covid-19 restrictions, and Winskill admitted: "It's even been bizarre for the lads during the season; we normally have anything between 50 and 150 people coming to watch games, and this season there's been nobody.
"And certainly on an occasion like tonight it's something else that would add to the spectacle and experience for the lads if they've got a crowd there and they've got family and friends in the crowd watching them. So that will be a miss for them - but once the game starts, the fact that they're in the stadium and playing on the pitch, and representing Newcastle... the game's the game."
Paul Gascoigne was part of the talented Newcastle side which won the FA Youth Cup in 1985, while more recently the likes of Sean and Matty Longstaff, Freddie Woodman, Adam Armstrong, Paul Dummett and Andy Carroll have caught the eye in the famous competition before making their names in the first team.
And Winskill added: "Matty and Sean came into the Academy last season and spoke to the lads, did a question and answer with them, which was fantastic. The lads were asking them about their experiences in the Youth Cup, and I always remind them they're following in the footsteps of lads who have been through this pathway and have come out the other end, and are now playing in our first team in the Premier League.
"That's what they aspire to do and that's the inspiration that we draw, that it's possible. These opportunities are a great chance for them to impress whoever's watching, to push them along their journey, their pathway."
Winskill's own pathway saw him join Newcastle as a 16-year-old full-back in 1993, before his release two years later led to him embarking upon a successful coaching career shortly afterwards, but the FA Youth Cup games remain among the most memorable of his playing days.
"It was a big competition, they were big games," he recalled. "They were ones where you had to control your nerves, go and perform as you had done during the season - albeit you had a big stadium surrounding the pitch. It was about playing the game and not the occasion.
"Something I keep saying to the lads is, it's about making memories. This group that we have playing tonight, I've been with some of the lads for four, five years - Elliot, Joe White, Josh Gilchrist, Nathan Carlyon, Lucas de Bolle - and we've had some great memories over the years. We've won tournaments in France, in Poland, we got the to the final of the Premier League Floodlit Cup, the final of the SuperCup in Northern Ireland last season.
"Across your football career and your coaching career, those are the big memories that stick with you, good and bad. Those are the things that when you finish your football career and you're coaching, or doing whatever you're doing, you can go back to when you bump into those players later on in life.
"Now I bump into Stuart Elliott quite a bit, who played in the youth team with me; Paul Brayson, Paul Barrett, and when you meet up with those players, it's those occasions that you talk about."
Midfielder Anderson, who regularly trains with the first team and signed a new long-term contract with the club on his 18th birthday last month, will be determined to show his quality against the teenage Terriers, with Winskill adding: "Over the last six months, he's really kicked on and he's the role model for the group now in terms of what's possible.
"And he's back tonight, playing with his mates, playing with the group that he's been with since he was nine, ten years old. I know he's been desperate to play in it and he's really looking forward to it.
"It'll be a big boost to the lads to have him back - like getting the old gang back together. He's a really talented lad and he's popular among the group as well. We've been to a lot of tournaments in the past where he's been a key figure. Other than that, we're at practically full strength, so we've got a big squad to pick from.
"We are expecting a tough game, we don't underestimate anybody and we always treat the opposition with respect and go about playing our way regardless of who the opponent is.
"But the carrot is, if we can get through to the next round there's a chance we could play at St. James' Park. From my point of view and theirs, it would be a real honour to walk out at St. James' Park in the next round, so that's what's at stake and we've got to go and achieve that."
