Jose Mourinho suffered an unwanted career first when his side went down 1-0 to Everton in their opening game of the Premier League campaign.
Dominic Calvert-Lewin headed past Hugo Lloris 10 minutes into the second half to consign Spurs to a defeat.
It is the first time in Mourinho's 20-year coaching career that the Portuguese has started the league season with a loss.
The 57-year-old had a record of 11 wins and seven draws in his sides' first league matches of the season before the Toffees got the better of them in the Tottenham Hotspur Stadium.
In the Premier League, it is just the second time a Mourinho side has dropped points in their maiden game, with Swansea the only other team to come away with a point when they drew 2-2 in 2015-16.
While opening day defeats may be rare for the former Real Madrid, Inter and Manchester United boss, the north London outfit have had more of their fair share of them. Although it was the first time in five years that Spurs have lost on matchday one, only West Ham have begun more Premier League campaigns with a defeat, having been bested 14 times.
Mourinho was infuriated with the way his side conceded against the Toffees, complaining that the ball should have been moved back a few yards before Lucas Digne sent the free-kick into the box for Calvert-Lewin.
"The goal shouldn't be possible when you have six referees and VAR - to let a free-kick be taken five or six metres in front because it's a huge difference." he said.
Spurs, who finished sixth and 40 points adrift of champions Liverpool in the Premier League last term, have a chance to get back to winning ways on Thursday when they meet Lokomotiv Plovdiv in the Europa League qualifiers. They will then return to domestic duties with an away game against Southampton on September 20.