Harrogate Town's Academy side suffered stoppage time heartbreak in Round One of the FA Youth Cup as Stockport struck a 93rd minute winner to secure a 2-1 win at The EnviroVent Stadium.O'Boyle wasted no time in putting Town ahead, collecting possession and firing a low left footed shot past the County 'keeper after just three minutes.
Town had made a good start, but a lengthly stoppage to Stockport's Lee Williams took some of the pace out of the contest and paved the way for the visitors to equalise.
Ashton Mee grabbed the goal after being in the right place at the right time to dispatch a low cross from the right, with Cadarn Taylor almost blocking the effort.
Town nearly responded in fine fashion two minutes later as Ollie Nicholson's sweetly struck free kick came down off the bar and bounced clear, but Town went into the break level with their Category 3 academy opponents.
Both sides had chances at the start of the second half with Harvey Giles making three saves before the hour mark to deny County and Emmanuel Ilesanmi going close at the other end.
A couple of Keane Barugh free kicks threatened to put the visitors ahead, but the first effort bounced back off the bar and the second was kept out by Giles.
Bobby Attree went close with a header in the 78th minute but, despite late chances for both, it would be Stockport who snatched a place in the 2nd Round as Luke Partington squeezed the ball in at the near post in the 93rd minute.
Town: Giles, Taylor, Moorby, Lee (Wilson 59), Attree, Smalley, Nicholson, Liddle, Ilesanmi, O'Boyle, Brodella (Samuels 74)
Subs not used: Mooney, Kerr, Birmingham, Williams, WIlson
Goals: O'Boyle 3
Booked: O'Boyle, Nicholson
Stockport: Blake, Partington, Jones, Kenny, O'Brien, Barry (Fligg 85), Barugh, Johnson, Omoruyi, Mee, Williams (Macfarlane 17)
Subs not used: Harrison, Stokes, Bryning, Whittle, Bradbury-Allen
Goals: Mee 33, Partington 90+3
Referee: Matthew Langdon