Last October, while in charge of Chelsea, Villas-Boas's team led twice, and were drawing 3-3 with 10 minutes to go, only for Robin van Persie to seal a hat-trick with two late goals which earned the Gunners a 5-3 victory.
Jose Mourinho never lost a single league game at home during his three years at Chelsea. Villas-Boas didn't make it three months. Perhaps it is no surprise that, by the time the reverse fixture rolled around the following April, the Portuguese was out of a job.
Villas-Boas comes up against Wenger again on Saturday, only this time he is taking his Tottenham side to face their local rivals on their turf. In his short time at the club—which has featured a first league win at Old Trafford but also disappointing defeats to Newcastle United and Wigan Athletic—it has already been impressed upon the young coach how important the north London derby is. Villas-Boas said (via ESPN FC):
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"[Spurs chairman Daniel Levy] keeps on mentioning it! But it's normal. We really have to embrace it because it's part of the great English culture of this game. Against Arsenal, for both teams, it means a lot. The meaning of it is quite special and all of us embrace it.
"I have been getting it for the last two weeks. People have been speaking about it quite often, the staff and the chairman, so you understand the importance of it. This is a game where passion is extremely high. It represents three points but it means more."
While Tottenham's 35-year-old coach is entering into his first derby, his 63-year-old counterpart is about to take charge of his 39th in all competitions since his first in November 1996, a 3-1 win at Highbury secured with goals in the final minutes from Ian Wright and Dennis Bergkamp.
In that time, Wenger has won 17 of those games—including a 2001 FA Cup semifinal, a crazy 5-4 win at White Hart Lane in 2004 and coming from 2-0 down to win 5-2 at the Emirates last season—and lost just five.
However, four of those losses have come in the last five seasons, and one each in the last three, most notably a 5-1 thrashing in the League Cup in 2008 and when Spurs themselves themselves came from two goals down to win 3-2 at the Emirates in almost two years ago to the day.
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"My chairman doesn't need to ring me to tell me how important this fixture is, he knows what it means to me. I have played this fixture for 16 years now and know what it means. It is always a frantic game and in recent years, we have had many goals."
But the Gunners are enduring a mixed season themselves, with a limp defeats at Norwich in the league and at home to Schalke in Europe coming before letting two-goal leads slip twice in their last two games to Schalke (again) and Fulham.
What will the result be in Saturday's north London derby?
The two bosses may be at opposite ends of their careers, but they are currently suffering from similar problems at both ends of the field. Spurs travel to Arsenal with the clubs sitting seventh and eighth in the table respectively, and each club has scored just 18 goals in their 11 league games thus far. Arsenal have conceded 12 goals in their last four matches in all competitions, while Spurs have only kept one clean sheet in the league this term.
It remains to be seen whether old hand Wenger or the man nearly half his age will be the one to find the solutions on Saturday afternoon. Then again, considering this fixture has produced more Premier League draws than any other (17), this match may not be the best place to find out whether youth is more important than experience.
But with a total of 32 goals scored in the last seven north London derbies, it should be a lot of fun putting these attributes to the test.