Tamir Cohen's dramatic last minute goal ended Arsenal's fading title hopes as Bolton won 2-1 at the Reebok Stadium on Sunday.
Robin van Persie had cancelled out Daniel Sturridge's seventh goal in nine league appearances but, despite bombarding the Bolton defence, Arsenal could not find the winner which would have kept their season alive.
Instead, they were caught out at the back in the dying moments as substitute Cohen pounced at the near post to break Arsenal hearts.
Arsene Wenger's side are now nine points behind leaders Manchester United with just four games to play.
And even if they defeat United at the Emirates Stadium next Sunday, Arsenal will have given themselves too much to do.
This was a must-win game as far as Arsenal were concerned and Wenger's team started as though they meant business.
A sweeping sixth minute involving Jack Wilshere, playing against the club he turned out for on loan last season, and Theo Walcott provided Cesc Fabregas with an early opportunity.
But the Arsenal captain fired high and wide of the target and the chance was wasted. It was the story of their half.
Jussi Jaaskelainen produced a fine stop to deny Fabregas from 20 yards in the 15th minute, while Matt Taylor was fortunate not to concede a penalty after his late challenge on Walcott.
But Arsenal were lucky to escape when Sturridge split the visitors' defence with a 25th minute pass which sent Lee Chung-Yong clean through.
The South Korean should have at least tested Wojciech Szczesny but instead attempted a fancy flick to Kevin Davies which came to nothing.
In a see-saw encounter, Samir Nasri wasted another opportunity when he missed the target from 20 yards after the Bolton defence had opened up.
But the hosts took the lead seven minutes before the end of an entertaining first half.
Moments after Szczesny had spread himself to deny Lee, Sturridge pounced from the resulting corner, the 21-year-old the first to the rebound after Gary Cahill's header had been cleared off the line by Nasri.
With their title hopes rapidly fading, Arsenal responded through Fabregas who hit the woodwork from 25 yards.
Yet it looked all over for Wenger's side when Sturridge went down inside the area following Johan Djourou's 47th minute challenge.
Referee Mike Jones immediately pointed to the penalty spot, a harsh decision as Djourou made the slightest of contact.
However, justice was done when Davies's poorly struck penalty was kept out by Szczesny.
Seconds later Arsenal were back on level terms after Fabregas's surge forward resulted in Van Persie finding the net from the edge of the area.
Arsenal bombarded the home defence in search of the winner but were sunk when Cohen, who celebrated by taking his shirt off to reveal a picture of his late father Avi Cohen, pounced with a close range header.
Arsenal have now won just one of the last seven league games and are on the brink of a sixth successive season without silverware.