The stage was set and Dempsey strode on as a starter, with 90 minutes laid before him and an open invitation to justify Spurs' summer investment—that and answer the impatient fans who are already doubting his worth.
It didn't happen. Dempsey barely impacted the match and disappeared altogether for long periods of it. Of Spurs' starters, only Aaron Lennon—out wide in a game that was played mostly in central areas—had fewer touches.
Dempsey supporters won't like to hear it, but the game passed him by. You certainly didn't hear that many times last season, when "Deuce" was banging them in for Fulham and playing like a man possessed.
The U.S. international just couldn't find his place on Sunday. And when you look at the numbers, Dempsey's diluted influence as a second striker was further evidence of his unconvincing start to life with Spurs.
Last season, Dempsey averaged 3.9 shots per game in the Premier League. He's averaging just 1.8 for his seven league starts and one substitute appearance this season.
It's still early, but some might even look at his goals column. Dempsey has two from 11 starts. Last season, he scored at a rate of nearly a goal every other game.
ESPNFC's Tottenham blogger is already asking the question, "Is Clint Dempsey good enough for Spurs?"
His conclusion is no. And he's not the only one.
In my opinion we pretty much played with 10 men today. Dempsey offers absolutely nothing. Others were also poor, but he is consistently bad.— Mitchell Pyman (@MPyman) November 11, 2012
Back from Manchester. Disappointed with the result and attacking performance. Can't work out what Dempsey does and Lennon was very poor— Sam Goldman (@samgoldman91) November 11, 2012
#thfc are really struggling to create anything through the middle - mostly because Dempsey's been poor. No10 position is a real issue.— Ben Pearce (@BenPearceSpurs) November 11, 2012
Football fans are notoriously quick to judge when their team is beaten, but anti-Dempsey sentiment had surfaced before Sunday's game. Some Tottenham fans just aren't convinced he's a player who makes them better.
To be fair to Dempsey, he's adjusting to a new club, with a new manager. The much-talked about "settling in" period is in session, and Dempsey was always going to need time to adjust to everything (tell that to Robin van Persie).
Dempsey's popularity in Spurs ranks was not helped by the fact he started and Jermain Defoe didn't against City—despite the striker having scored a hat-trick midweek against Maribor.
Spurs manager Andre Villas-Boas went with his preferred 4-2-3-1, using Emmanuel Adebayor as the lone striker and Dempsey behind him. In the buildup to the match he talked about Dempsey's "amazing run of games," suggesting he is quite happy with his new signing's contribution.
But AVB's tactics didn't do Dempsey any favours against City. As the middle man of three, he was overwhelmed by City's spine, and barely had time to blink without somebody closing him down.
Lennon and Gareth Bale, on either side of him, rarely came to his assistance. Lennon hugged the right touchline, while Bale drifted naturally to his left. You might argue 4-2-3-1 was actually closer to 4-4-1-1, which played right into City's hands.
Compare Spurs' action areas with Chelsea's against Liverpool, and you'll see the difference in how the their respective threes behind a striker operated. Oscar, Juan Mata and Eden Hazard stayed narrow for Chelsea, supporting each other in attack and defence. Dempsey, meanwhile, was left to fend for himself (graphics as per FourFourTwo's Statzone App).
That alone doesn't justify Dempsey's poor performance, but it explains in part why he struggled to make himself known. He was effectively one man against four in that part of the pitch, up against City's two central defenders and their two holding midfielders.
For Villas-Boas to get the best out of Dempsey in a 4-2-3-1 he needs to employ a different approach—either use him on either side of the three, or use him centrally to ensure the other two players stay closer to him.
Dempsey needs greater freedom to thrive and a system that gets him on the ball in advanced areas, which simply didn't happen enough against City.
For all his much-vaunted versatility, Dempsey has always been at his best going forward. If Villas-Boas wants somebody to work deeper, Moussa Dembele is a better option, and he'll be back soon enough.
But who's to say Dempsey and Dembele can't both thrive in the same team? Both played as Fulham beat Arsenal 2-1 at Craven Cottage last season, and Dembele may well be able to provide more support from behind Dempsey than Tom Huddlestone and Sandro managed on Sunday.
Most of all, Spurs fans need to be patient. Dempsey proved his class last season and it's up to Villas-Boas to unlock that potential and find the right formula for success.
Where better to start than the Emirates?