YORK City began their new era of ownership with a 3-2 home loss against Sky Bet Championship side Middlesbrough in their first of six pre-season friendlies.

Goals from Sonny Finch and Calum Kavanagh, the latter scoring a brace, ensured that Manny Duku’s 70th minute header and a late Daniel Dodds own goal were rendered irrelevant.

In spite of the loss, the atmosphere at the LNER Community Stadium seemed upbeat, with almost 3,000 City fans in full voice to introduce a new era of the club led by Glen Henderson.

Henderson was named as the club’s new chairman on Tuesday, taking over a 51 per cent stake to become York’s majority shareholder.

The new chief will work closely with City’s Supporters’ Trust, who hold the remaining 49 per cent.

It was an evening of many debuts for York, with nine players featuring in what was their maiden game for the club.

Ethan Ross, Adam Crookes, Gus Mafuta, Scott Burgess, Scott Boden and Luke James all started the game, making their first appearances for City.

Left-back Alex Whittle also started the game in what was his first match for the Minstermen since 2018.

The 29-year-old spent two seasons with York between 2016 and 2018 before departing for Forest Green Rovers, who were then in the Sky Bet League Two.

It was hardly an idyllic start for City when, just five minutes in, they found themselves down by a goal.

Centre-back Sam Sanders dealt with an incoming ball poorly which allowed Josh Coburn to break through the defence.

He played the ball across to Sonny Finch who, unmarked and five-yards from an open goal, couldn’t miss.

The Minstermen were deploying a back-five for much of the first half, with Whittle and Olly Dyson playing as wing-backs on either side of Maxim Kouogun, Sanders and Crookes.

Despite the defensive reinforcement, they struggled to contain the persistent attacking waves that Middlesbrough were creating.

After just over 15 minutes had been played, Dyson made a poor pass backwards that Riley McGree latched onto.

He was able to unleash a shot on goal, but saw it valiantly blocked by Sanders.

City’s first move that could be considered even a half-chance came just moments later, when Mitch Hancox surged forward from the midfield.

He found James who was able to play Dyson down the wing, but the versatile player’s cross was sent over the bar.

Goalkeeper Ross, who had a shaky opening five minutes, really came into his own as the first half progressed.

McGree again found himself in the York box and went for goal, being one-on-one with City’s loanee goalkeeper.

Ross though produced a brilliant, acrobatic save to prevent the Australian international doubling his side’s lead.

The 25-year-old was called into action once again only minutes later, making an impressive double save at point-blank range to yet again keep the deficit at just one goal.

York really struggled to create much when they looked to attack. They seemed reliant on long balls forward that, more often than not, were read and intercepted by a ‘Boro defender.

Thankfully for the Minstermen, Ross was on form. The goalkeeper, who joined City on loan from Stockport County, made seven saves in the first half to keep Middlesbrough’s rampant attack at bay.

The second half saw the introduction of Fraser Kerr, Manny Duku and Alex Hurst, who were making their debuts for the club.

Ryan Whitley, Lenell John-Lewis, AJ Greaves and Maziar Kouhyar also took to the field for the second half, as did a trialist.

Later in the half, academy graduate Ben Dale would make his debut for the club, coming on in place of Dyson.

City began the second half brightly, far more lively than they seemed in the opening stages of the first 45 minutes.

The substitutes all made an impact on the game, with Hurst and John-Lewis having a particular influence.

The attacking duo combined well, with John-Lewis often bringing the ball down and finding Hurst down the left wing.

One such move saw Hurst, who was named as chairman Henderson’s man of the match at the end of the game, fire in a dangerous cross that went narrowly wide of the post.

In spite of York’s better efforts, Middlesbrough would eventually double their lead.

Just moments after Duncan Watmore missed a golden chance for the visitors, Kavanagh got his first of the game.

He found himself with the ball at his feet after two shots had been blocked in quick succession. Kavanagh was faced with an open goal and, similar to Finch in the first half, could not miss.

City’s efforts were eventually rewarded when, after 70 minutes had been played, Duku rose and headed an effort into the goal.

It was a tremendous header that saw York back in the game, their much changed 11 applying a pressure that was seemingly lacking before the rearrangement.

Though York were able to maintain their intensity, Middlesbrough were still able to showcase their quality.

After almost three quarters of an hour had been played, Marcus Tavernier saw a shot well saved and could only fire his rebound onto the post.

Moments later, Tavernier had yet another shot which Whitley once again saved. The ball rolled under the York keeper before being cleared off the line.

With just over five minutes left to play, ‘Boro came forward once again. The ball was hit into the box and found the head of Kavanagh, who was able to score his second of the game. Whitley was unable to keep his header out.

As the game entered the dying embers, a cross was fired into the Middlesbrough box.

It sailed over John-Lewis’ head, but bounced off Daniel Dodds and trickled into the goal. Though it was too little, too late for City, it was a nice way to end an introduction to a brand new era for the club.

York: Ross (Whitley 45'), Kouogun (Kerr 45'), Sanders, Crookes, Mafuta (Duku 45'), Dyson (Dale 84'), Burgess (Greaves 45'), Hancox (Kouhyar 45'), Whittle (Hurst 45'), Boden (John-Lewis 45'), James (Trialist A 45')

Subs: Whitley, Kerr, Greaves, Duku, Kouhyar, Trialist A, Hurst, John-Lewis, Dale (all used)

Star man for York: Alex Hurst. He won man of the match and did so for a reason. Hurst pressed Middlesbrough brilliantly when he was on the pitch and often looked to be the outlet for City attacks.

Goals: Duku (70’), Dodds own goal (89’)

Stats for York | Middlesbrough:

Shots: 2 (2) | 21 (15)

Corners: 3 | 7

Offsides: 0 | 2

Fouls committed: 9 | 11

Attendance: 4,198 (1,310 away fans)