Boro’s unbeaten pre-season came to an end after being edged out at York City.
Dael Fry had given Neil Warnock’s side the lead, but the home side replied with two of their own before half-time as Boro fell to the same opponents that had beaten Newcastle United last week.
The game was notable for the first start of the summer for Jonny Howson and a first senior Boro appearance for experienced defender Sol Bamba, who has been training hard with the squad at Rockliffe.
It took just six minutes for Boro to take the lead. Paddy McNair swung in a free-kick from deep and Fry got up well to head the ball beyond the reach of Peter Jameson in the York goal.
It was almost two when Jamie Paterson finished off a fine move by heading against the bar. It started with Howson Uche Ikpeazu delivered a fine cross, Matt Crooks headed it back into the danger zone, and Paterson was only denied by the woodwork.
Crooks was next to go close after when was denied by the hand of Jameson following an incisive pass to release him on goal from Sam Morsy.
York were back on level terms before the half-hour though when Mackenzie Heaney was able to seize on a half-cleared ball and volley it home sweetly, leaving Joe Lumley with no chance.
And the home side got their noses in front before half-time when Scott Barrow sent in a great ball from the left and Mark Beck’s glancing header was well placed into the bottom corner.
Boro had an opportunity to restore parity shortly before the hour, but Jameson saved a McNair penalty with his legs after Ikpeazu’s persistence and strength brought about the foul for the spot-kick.
As the game passed the hour-mark, Warnock reshuffled his pack completely, making eight changes to add to two earlier substitutions leaving Djed Spence as the only starter still involved in the game for Boro.
The changes saw a first senior involvement for the experienced Bamba and marked a return for striker Josh Coburn, fresh from scoring for the U23s last weekend.
Boro pushed for a leveller with York getting in some vital blocks and challenges during the closing stages. The home side also had a chance themselves with five minutes left when an overhead kick flew just wide.
Boro: Lumley (Stojanovic 65), Dijksteel (Peltier 85), Spence, Hall (Wood 65), Morsy (Robinson 56), Fry (Bamba 65), McNair (Hackney 65), Paterson (Jones 46), Crooks (Coburn 65), Howson (Malley 65), Ikpeazu (Akpom 60).