Video: York City 3 Middlesbrough 3 (0-3 pens)
York City's reserves fought back to within seconds of a North Riding Senior Cup final appearance before eventually losing a penalty shoot-out to Middlesbrough's Under-23s.
Mikael Soisalo handed the visitors an interval advantage that was cancelled out by Clovis Kamdjo's unopposed header midway through the second-half.
But substitute Stephen Wearne soon had the hosts once again chasing the game, only for City's youth-team midfielder Harry Thompson and Matthew Elsdon's own-goal to leave them firmly in the box seat.
However, Stephen Walker equalised after Luke Simpson had initially blocked his stoppage-time penalty, with Boro counterpart Brad James similarly denying Raul Correia, Josh Law and Aaron Haswell during the shoot-out.
Video Link: YorkCityTV