I agree, it seems strange to me that we have so many good enough to get games in the first team, but we can't seem to get very far in the youth cup..
Having watched a few of the youth cup games and some of their league fixtures in recent years, I think the problem in terms of success probably comes from what each side wants from the fixtures.
Whenever I've seen Town play it's more about the development. You can see that there's a style and a philosophy in how Neil Woods sets his sides up. I'm not saying they're not playing to win but it's clearly with an eye on developing those players to play first team football.
I'm going to use an example of Mansfield who we played and lost against in one of the youth cups a few years ago. Mansfield as a footballing side were bloody dreadful. Nothing at all about them and not a single one of their players looked capable of making the step up into the mens game, technically just devoid of anything.
Town on the other hand looked very slick, fluent and organised. It's always hard to say this player could step up and this one couldn't, but no-one looked out of place. First half Town absolutely dominated and led comfortably. There was only going to be one winner at this stage.
Half-time Mansfield responded by putting on an absolute bruiser up front. He made Matt Rhead look slender and mobile. This lad had about as much chance of making it as a professional footballer as I do. But what he did do was bully the Town lads in defence, which included Mattie Pollock. Mansfield went big boot with a man-child playing against children. It worked and Mansfield won in the end. Mansfield might have got through to the next round but their players probably didn't benefit from that game. At that moment in time, a physical approach to the game like that would be too much for the Town lads who are still growing. As they get stronger they'll be able to cope better with it.
The Mansfield lads might benefit from that approach against young lads, because they definitely had that physical advantage, but in the mens league that advantage is redundant. They've also gained nothing in terms of technical development.
This is the case in a lot of the league games I've seen too. Town don't seem as big or strong but the emphasis is more on giving them the technical skills, knowing that the physicality will come in time. Whereas other clubs go for the biggest, strongest lads who might be dominant until about 18 but once everyone else catches up they actually get left behind.