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.
9. Matt Crooks - 5
Operated in one of the advanced midfield positions behind Ikpeazu. Made a few runs behind the York defence but spent most of the game on the fringes. 5 Photo: Getty Images
10. Jamie Paterson - 4
Headed a first-half effort onto the bar but struggled to make an impact as he was subbed at half-time. 4 Photo: Getty Images
11. Uche Ikpeazu - 7
Made some probing runs into the channels and held the ball up when it came to him. Won a penalty but lacked support up front. 7 Photo: Catherine Ivill
12. Isaiah Jones - 6
(for Paterson, 45) Looked bright when he came on with some direct runs on the left. Final ball let him down at times. 6 Photo: JPI Media