Arsenal failed to beat Thierry Henry's New York Red Bulls after a late Kyle Bartley own-goal handed the MLS side a 1-1 draw which wins them the Emirates Cup.
A first-half Robin van Persie header at Arsenal's Emirates Stadium home put the Gunners ahead before substitute Bartley's attempted clearance of a Juan Agudelo cross cost his team the victory, with former Gunners superstar Henry creating the chance.
Unsurprisingly it was the home side that dominated possession from the off, and continued to do so for the duration of the game.
Their play patterns were disrupted slightly in the seventh minute however as Jack Wilshere was forced off with an ankle injury and replaced by 18-year-old Benik Afobe.
It was the Red Bulls who had the first real shot on goal through man of the moment Henry, his effort forcing Wojciech Szczesny to scramble to his right - but it was always sliding wide of the post.
Arsenal had half chances through Van Persie and Aaron Ramsey as they tried to break the Red Bulls down, but it was Henry who again came closest to breaking the deadlock.
The Frenchman won a free-kick on the edge of the 'D' and stepped up to take it himself; his curling strike towards the near-post top left corner forced Szczesny into a flying save.
Despite the chances, Arsenal were dominating the play and Ramsey had a great chance on 27 minutes. A Kieran Gibbs shot was parried by Franck Rost and the Welshman pounced, but his volley was over the bar when he really should have scored.
The home team were surprisingly denied a penalty just a minute later when Gervinho dispossessed Chris Albright in the right-back position. He was in on goal before the Red Bulls defender hacked him down from behind.
The Ivorian's touch had been heavy and Rost may have been able to claim the ball from him, but it was without doubt a foul.
Arsenal really started to press for the opener and were rewarded for their aggressive play on 42 minutes when Van Persie got his name on the scoresheet.
Tomas Rosicky swung a free-kick from the left wing on to the head of his captain, who beat Rost to the ball and saw it bounce into the open goal.
Gervinho nearly made it two a minute later when the impressive Rosicky slid him in behind the defence. The new arrival took too long to strike and Rost closed the angle and made the block
The second half settled back into the pattern of Arsenal dominating possession and territory, but they had lost their aggressive edge and failed to create chances.
Rost was barely tested and the longer Arsenal went without scoring a second, the more it seemed they might regret it. The two main attacking threats of Gervinho and Van Persie were substituted in the 65th minute to end any hope of a cutting edge.
Red Bulls meanwhile never gave up and handed the Gunners a warning shot with 20 minutes to go when Henry found space and curled in a shot from the edge of the box which Szczesny held well.
Arsenal were made to pay in the 84th minute. Red Bulls won a corner which they played short to Henry; he held up the play well, waiting for the run of Agudelo, whom he then played in with an inch-perfect pass.
Agudelo surged to the byline and fired a ball across the six-yard box which was impossible to defend - Bartley could do nothing but put through his own net.
Arsenal were shell-shocked and in the remaining moments could not create anything, the game petering out to end in a draw.
Arsenal were booed at the final whistle. Their fans fear the same problems will reoccur next season: they have no problem dominating a game, but winning is a different matter. This is the first time they have failed to win the pre-season Emirates Cup in three years.
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