Frustrating time for Wenger

Arsene Wenger endures mixed feelings as Arsenal maintain their proud record against Tottenham.

Tottenham Hotspur's Benoit Assou-Ekotto, left, tussles with Arsenal's Robin van Persie during their goalless North London derby draw.

Arsene Wenger endured mixed feelings as Arsenal maintained their proud record against Tottenham. A red card for Emmanuel Eboue in the 38th minute forced the 10-man Gunners to grind out a draw against their rivals, who had not beaten them in the Premier League since 1999.

But a point was not what the Frenchman wanted in the tense fight for a top-four spot. They are now five behind Chelsea and seven adrift of Aston Villa and are now in serious danger of missing out on the Champions League next season. It took just over 60 seconds around the 36th-minute mark for Arsenal's fortunes to change. If the sight of Emmanuel Adebayor - the scourge of Spurs with eight goals in eight games against them - hobbling off with a suspected hamstring injury was not bad enough, Wenger must have been dumbfounded as Eboue joined him down the tunnel almost immediately. Two yellow cards, two moments of stupidity that let down his teammates and his manager.

The first came for dissent when he continually disputed a free-kick decision, and the second when he needlessly tripped Luka Modric while on the floor after the Spurs midfielder had barged into him. Petty, but the referee, Mike Dean, had little choice but to make him the 76th player to be dismissed under Wenger's charge. The Arsenal manager should be similarly unforgiving to a player whose antics spoil his potential. There was no excuse for his actions, even if he had been wrongly denied a goal earlier. He drilled a 13th minute effort into the net, but he and Arsenal were unlucky as Adebayor was adjudged to have fouled Jonathan Woodgate just before Eboue struck.

Spurs could point to a penalty being rejected at the other end when William Gallas seemed to catch Robbie Keane. All eyes were on the Irish striker as he made his return to the club following his unhappy spell at Liverpool, but he had little chance to make it a third goal in successive games against the Gunners. A close-range header in the 57th minute that whistled over was the closest he came in a derby game that had much energy and effort, but ultimately few clear-cut chances.

"We wanted the three points and when they went down to 10 men we didn't take advantage of that, so it's a bit frustrating," said Keane. "We were pushing for the whole game, but couldn't break them down." Modric, inventive throughout, almost snatched victory in injury time when Manuel Almunia made a crucial block. But Arsenal battled superbly and almost pinched victory themselves. Alex Song dragged a close-range effort wide before Carlo Cudicini tipped over a drive from Nicklas Bendtner in a frantic finale.