On April 14 2001, Middlesbrough beat Arsenal 3-0 at Highbury.
It was just one of eight losses Arsenal experienced in the Premier League that season and they still managed to finish second, albeit 10 points behind title winners Manchester United and only one point above Liverpool in third.
Just three days after beating Manchester City 4-0 at Maine Road, the Gunners suffered a 3-0 defeat in front of their home crowd thanks to own goals from Edu and Sylvinho just four minutes apart in the first half, and a goal from Hamilton Ricard in the second.
It was the last match in which Arsenal failed to score at Highbury until 30 November 2003 when they drew 0-0 against Fulham during their Invincible season.
After Arsenal’s defeat to Boro in 2001, they would go unbeaten in the league until the final day of the season when they lost 3-2 away to Southampton.