A goal in added time from Nicklas Bendtner saw sent ten-man Hull City to a 2-1 defeat against Arsenal at the KC Stadium on Saturday evening.
Jimmy Bullard's penalty had cancelled out Andrey Arshavin's early opener, but despite a great team effort following George Boateng's sending off on the stroke of half time, it was late heartbreak for the Tigers as Bendtner punished Boaz Myhill's failure to hold Denilson's long range shot.
Phil Brown made six changes to his side for the clash. Andy Dawson returned from illness to slot in at left back in place of Kevin Kilbane while on the right side of defence, Bernard Mendy came in for Paul McShane.
Elsewhere, Nick Barmby, Tom Cairney, Richard Garcia and Amr Zaki dropped out of the side to be replaced by Dean Marney, Craig Fagan, Jozy Altidore and Jan Vennegoor of Hesselink.
City started with a 4-4-2 formation with Marney playing on the left.
A good turn from Altidore saw him get away from Sol Campbell in the third minute, but he dragged a shot wide from 20 yards.
Arsenal took the lead on 14 minutes after a slick passing move. Bendtner fed Arshavin and after running through two City defenders, he finished past an exposed Myhill.
City were struggling to get back into the game, but they were awarded a penalty on 28 minutes when Campbell brought down Vennegoor of Hesselink in the box as the striker looked to finish Marney's clever flick. Campbell was booked when he probably should have been sent off and Bullard smashed the spot kick into the top corner of the net.
That was one of the few decisions that went City's way in a first half when referee Andre Marriner got things wrong time and time again, although he was right to book Dawson for a late tackle on Denilson. George Boateng and Bendtner were also shown a yellow card apiece after confronting each other after Dawson's challenge.
And it proved costly for Boateng as he was sent off in added time after a high challenge on Bacary Sagna.
Half Time: Tigers 1-1 Arsenal
City fans were up in arms five minutes after half time following Campbell's strong challenge on Kamil Zayatte, but the Arsenal defender did get plenty of the ball. Either way, the challenge left Zayatte needing lengthy treatment, and although he eventually limped back into the action, he soon went down again and was replaced by Liam Cooper.
For the record, City were now playing a 4-4-1 formation with Altidore dropping onto the left of midfield and Marney moving inside to cover for the absence of Boateng.
Bullard went close for the Tigers on 66 minutes with a 25-yard drive that went just over the bar.
At the other end, Arshavin missed a golden chance when substitute Theo Walcott's low cross found its way into his path. The Arsenal man blazed high and wide when unmarked, although he will no doubt claim the ball bobbled off the patchy KC Stadium surface.
Bendtner also had a chance when Dawson's header fell at his feet, but he fired over under pressure from Steven Mouyokolo.
City's second change saw Garcia replace Vennegoor of Hesselink. Altidore moved back up front with Garcia playing out wide.
Mouyokolo put Bendtner under pressure again on 80 minutes when it seemed the Arsenal man would have an easy strike at goal, deflecting the effort over the bar.
City's final change came with seven minutes to go as Kilbane replaced Altidore.
Eduardo's through ball looked to have sent Walcott clear on goal a minute later, but Cooper did well to put in a challenge and get the ball to safety.
As the game entered six minutes of added time, Arsenal set up camp in City's half and Myhill had to save from Gael Clichy, his first real save of the game.
City's resolve was finally broken a minute later. Myhill could only push Denilson shot into the path of Bendtner and he converted the rebound.
Tigers: Boaz Myhill, Bernard Mendy, Kamil Zayatte (Cooper 55), Steven Mouyokolo, Andy Dawson, Craig Fagan, George Boateng, Jimmy Bullard, Dean Marney, Jozy Altidore (Kilbane 83), Jan Vennegoor of Hesselink (Garcia 73).
Subs: Matt Duke, Liam Cooper, Kevin Kilbane, Seyi Olofinjana, Richard Garcia, Nick Barmby, Amr Zaki.
Arsenal: Manuel Almunia, Abou Diaby, Bacary Sagna, Thomas Vermaelen, Samir Nasri (Eduardo 76), Denilson, Gael Clichy, Andrey Arshavin, Emmanuel Eboue (Walcott 66), Sol Campbell, Nicklas Bendtner.
Subs: Lukasz Fabianski, Eduardo, Theo Walcott, Mikael Silvestre, Armand Traore, Fran Merida, Craig Eastmond.
Referee: Mr A. Marriner.
Attendance: 25,023.
