On Sunday, Antonio Conte returns to the place where his worst fears about Tottenham were realised for the first time. It was particularly galling for a former Chelsea manager that the scale of his task was made clear at Stamford Bridge of all places, as the Blues eased to a 2-0 win in the Carabao Cup semifinal, first leg in early January.

The scoreline wasn’t particularly savage, but Spurs conceded two dreadful goals and failed to register a shot of any description until the 50th minute in a meek surrender that left Conte unwilling to pull any punches in his post-match assessment. “There’s an important gap, an important difference, there’s a big job to do to retrieve the situation,” he said in assessing the distance between Spurs and the top sides.

Conte was barely eight weeks into the job, and he had already masterminded a draw against Liverpool and seven wins from his first 12 games in charge.

But the chastening nature of that defeat to Chelsea — followed by an equally insipid showings in the return leg and a Premier League defeat to the same opponents later in the month — began a series of public utterances which raised questions over whether he would even stick around. After losing to Burnley on Feb. 23, Conte publicly doubted whether he was the right man for the job.

Even after pulling off an improbable fourth-place finish by thrashing Norwich 5-0 on the final day of the season, he still refused to commit to remaining as Tottenham head coach amid concerns the club would not back him to the extent he felt necessary to turn Spurs into title challengers.

Conte knows enough about London to “mind the gap.” Optimism that this “gap” between them and the top clubs is finally closing comes from six summer signings, a full preseason working under the Italian and an encouraging 4-1 win over Southampton on the opening day. But Sunday’s trip to Chelsea represents the first meeting of the Premier League’s traditional Big Six this season, and will also offer the clearest indication yet whether Conte’s rebuild is on track.

Both Conte’s brilliance and his volatility are well documented. The 53-year-old is an elite manager, but has never spent more than three consecutive seasons at the same club, often leaving in acrimonious circumstances. Juventus were Serie A champions when he quit after one day of preseason ahead of 2014-15 following disagreements over the club’s transfer strategy. He was sacked from Chelsea in 2018 after falling out with the hierarchy and several senior players, again over the direction of the club. Conte departed Inter Milan last May in opposition to an unloading of top stars triggered by financial problems related in part to C-V-19.

There is a sense of optimism and hope at Tottenham, and Antonio Conte will look to keep the momentum going following a 4th place finish last season. CHRIS RADBURN / AFP

He did win four Serie A titles and the 2016-17 Premier League with Chelsea during this span, but his combustible personality always seemed an improbable fit with Tottenham, a club that has long prioritised financial prudence and long-term planning over short-term, boom-and-bust under the watchful eye of chairman Daniel Levy.

Conte’s unstable rhetoric around last season effectively built to a two-day meeting in Italy as the summer began and, together with the club’s football managing director, Fabio Paratici, they finalised a list of summer targets. Significant backing was required. Previous managers — perhaps most obviously Mauricio Pochettino — became disillusioned when failing to receive the support they felt necessary to take Spurs to the top, meeting a brick wall built from financial caution. This time, it was different. Levy and the majority shareholders, ENIC, agreed to help realise Conte’s vision for the future. It was a significant moment.

February’s departure of the club’s longstanding director of technical performance, Steve Hitchen, was a sign of Paratici’s growing influence, but here, emboldened by Conte guiding Spurs back into the Champions League, was a real sea change in Tottenham’s willingness to support their head coach.

Previously, players were signed with potential and a clearly defined future transfer market value. This time, they were in large part being targeted for the here and now. The arrival of 33-year-old wing-back Ivan Perisic embodies this shift more than any other signing. Spurs announced a £150m cash injection from ENIC that’s helped finance a spending spree with Perisic, Richarlison, Fraser Forster, Yves Bissouma, Djed Spence and Clement Lenglet arriving at the club.

This activity has generated a sense of momentum that quashed any concerns England captain Harry Kane could look for to leave the club — having tried to force a move away last summer — and, significantly, most of these signings were acquired early in the window, giving Conte a full preseason to work with his new players.

Conte’s training sessions are infamously tough. An agent of one player at the club told ESPN about double sessions involving tens of shuttle runs at the end. Another expressed surprise that Conte chose to work his players so hard in a session open to the cameras in Korea that Kane was sick by the side of the pitch, while others including Son Heung-Min could hardly stand during a brutal running drill. But the players have fully bought into Conte’s methods, in part seduced by his track record, and respectful of the level of control he clearly enjoys having been wholeheartedly supported by Levy in the transfer market.

ESPN has also been made aware of other data their coaches are using to explain the need to improve player fitness, including the high number of late goals Tottenham concede. If last season’s Premier League matches are broken down into 10-minute blocks, with each of the nine segments assigned an aggregate score based on goals scored and conceded in those minutes, Liverpool and Manchester City are the only sides ending with a positive score in all of them. Spurs had positive net scores in the first eight, but in those crucial final 10 minutes of matches, they scored seven and conceded 10, leaving them on -3. By contrast, City were +15 and Liverpool +14 in the final 10 minutes of matches last season; Chelsea were +8.

There are a plethora of reasons to explain this, not least the manner in which City in particular wear teams down with their level of possession, but it is one indicator which Conte is demanding greater intensity from his players for the entire game — they also fell behind in 17 league matches last season, a figure higher than Arsenal (15), Liverpool (12), Chelsea (11) and City (eight). Combined with Conte’s devotion to a 3-4-3 system, the players have been left under no illusions about the physical and tactical expectations placed upon them this season. Although it still remains a tall order on paper to match City and Liverpool, perhaps the biggest doubt over Spurs remains their ability to implement what is being asked of them under pressure.

The “Spursy” tag — a derogatory term essentially meaning “to falter with the winning line in sight” — is one the club have found difficult to shake. They were superb for the majority of the Pochettino era but ultimately ended his five-year stint without a trophy to show for the progress made. Their last success of any description remains the 2008 League Cup.

Jose Mourinho’s appointment as his successor was made with the idea in mind of fostering a siege mentality to galvanise the group, but he never achieved it. Nuno Espirito Santo’s 17-game tenure was a brief as it was unmemorable, and so Conte now finds himself charged with responsibility of changing this mindset. When asked in May whether he knew what “Spursy'” meant, he said: “I am trying to cut this.”

The only way is to win silverware. A smaller step on that path is improving Tottenham’s record away at the traditional Big Six. They have lost 37 of their last 60 league games away to Arsenal, Liverpool, City, Manchester United and Chelsea, winning only nine. Although Spurs beat City and drew at Liverpool under Conte, they have won just one league game at Chelsea since 1990 — a 3-1 victory in April 2018.

“Obviously when you face that kind of opponent [in Chelsea] it’s a good moment to judge yourself,” captain Hugo Lloris said after their opening-day win over Southampton.

Chelsea may have the proven pedigree but their summer transfer business is far from complete, and a new defence is bedding in after the departures of Antonio Rudiger and Andreas Christensen. There are certainly worse moments to play them.

By contrast, Tottenham have enjoyed a more settled preseason, building nicely from the last. Spurs improved considerably in the second half of last season, winning 10 of their last 14 league games to show a level of form, which prompted Conte to suggest he wished they could have another crack at Chelsea soon to see where they were at.

This weekend, he will finally get his chance.