I'd imagine most youth cup winning sides rarely see one or more make it into their first team to any notable degree.
The challenge we have now, is that a youth prospect breaking into a side that is challenging for the top 6 has a much harder time than one trying to break into the side in the mid-table or below, or even in the Championship. The very best will still make it, but players who are still more than capable of having reasonable premier league careers might never get a chance with us. I do sometimes wonder if Ramsey senior would have had the career he's had to date had he been two years younger and 'come of age' while we were upwardly mobile in the premier league. His breakthrough season, our second in the premier league, he appeared 20+ times, but was competing for a place on the pitch with the likes of Trez, Barkley, Marv, Anwar. Would he have got much of a look in if he was competing as an inexperienced 19-year-old with the likes of Bouba, Buendia, Diaby, Zaniolo, Traore, Bailey? Maybe, maybe not. Timing is obviously important, and carries a certain amount of luck, but I do think our youth products coming through today will face a MUCH bigger challenge even compared to those who cam through four or five years ago.