Boro were without a handful of first-team players against the non-league outfit, yet Neil Warnock was still able to name a strong side for the fixture.
Former Bristol City forward Jamie Paterson, who is on trial at the club, started his second friendly match for Boro after playing in the 2-1 win over Plymouth last week.
Defender Sol Bamba, who has also been training with Boro, came off the bench in the second half when the Teessiders made wholesale changes just after the hour mark.
Things appeared to be going to plan for the visitors when Dael Fry headed them ahead inside six minutes, yet goals from York duo Mackenzie Heaney and Mark Beck before half-time turned the game on its head.
Here’s how each Boro player fared.
1. Joe Lumley - 5
Left exposed for the goals. A few hesitant moments when clearing the ball. 5 Photo: Getty Images
2. Anfernee Dijksteel - 4
A rare off day. Looked a little rusty on the right, with both of York’s goals coming on his flank in the first half. 4 Photo: George Wood
3. Paddy McNair - 5
Delivered some inviting crosses into the box but failed to convert from the penalty spot in the second half. 5 Photo: Stu Forster
4. Grant Hall - 5
Beaten in the air for York’s second goal as Boro’s defence was breached twice in the first half. 5 Photo: Stu Forster