Daring to dream has been a dangerous art for Tottenham fans in years gone by, but the glass-half-full types were brimming with confidence that Conte could be the man to end their prolonged silverware drought, as the 2007-08 EFL Cup waits for its successor.
However, come May 2023, an all-too familiar sense of doom and gloom had arisen. From unprecedented managerial rants, vociferous protestations towards the owners, under-performing players and a sporting director scandal, Spurs always seemed to be making the headlines for the wrong reasons.
Here, Sports Mole takes an in-depth look back at Tottenham's turbulent 2022-23 season.
SEASON OVERVIEW
Final league position: 8th
EFL Cup: Third round
FA Cup: Fifth round
Champions League: Last 16
Top scorer: Harry Kane (32)
Most assists: Ivan Perisic (12)
Conte's necessity for financial backing was well-documented, and Daniel Levy blessed him with a summer spending spree in the wake of their return to the Champions League. The reserves were depleted on Richarlison, Yves Bissouma, Destiny Udogie and - perhaps regrettably in hindsight - Djed Spence, while Cristian Romero's loan from Atalanta BC was made permanent.
A host of unwanted names such as Tanguy Ndombele, Steven Bergwijn and Giovani Lo Celso were also cut from the ranks - mostly on loan - and Tottenham were in dreamland on the opening day of the season, picking up where they left off with a 4-1 demolition of Southampton to surge to the summit.
The Lilywhites were quickly usurped, though, and it took just two gameweeks of the new season for the first Conte flashpoint to emerge, as the ex-Chelsea boss squared to then-Chelsea boss Thomas Tuchel following a fiery 2-2 draw at Stamford Bridge, seeing red for his troubles.
Once the flared tempers had calmed, attention soon turned to the on-field Conte revolution. With 23 points from their opening 10 games of the season - including a seven-match unbeaten streak and one North London derby loss to Arsenal - Spurs had achieved their best start to a campaign for 59 years.
In that sequence, a solitary Kane effort at Brighton & Hove Albion saw the England captain become the first-ever player to score 100 Premier League away goals, and he dedicated his strike to late fitness coach Gian Piero Ventrone, who had died suddenly at the age of 62 a couple of days beforehand.
At this time, Spurs were largely struggling to make waves in the Champions League - winning just two of their opening five group games and being denied a last-gasp winner at home to Sporting Lisbon, landing Conte on the naughty step once again for another explosion of emotion.
However, with Cristian Stellini on the touchline, a dramatic Pierre-Emile Hojbjerg strike put Marseille to the sword on the final matchday to send Spurs through as group winners. Equally tense comeback wins over Bournemouth and Leeds United came either side of that success in France, as did more knockout disappointment in a third-round EFL Cup exit to Nottingham Forest.
Nevertheless, Spurs entered the World Cup break sitting pretty in the Champions League places - having only spent one week outside of the top four - but in the first few weeks of the New Year, Tottenham's well-oiled machine began to run out of lubricant.
Three of the Lilywhites' first four Premier League games in 2023 ended in defeat, and while those losses would have been painful for Conte, it would not have compared to the "severe abdominal pain" he suffered towards the end of January, as it was announced that the 53-year-old would undergo an operation to have his gallbladder removed.
As Conte recuperated, Stellini continued to weave his magic. Aiming to consign a difficult January to history, Spurs sunk champions Manchester City thanks to Kane's 267th Tottenham goal - surpassing the late Jimmy Greaves at the top of the club's all-time goalscoring charts, but Conte's side were still playing catch-up in the Champions League race amid their wholly inconsistent form.
The Tottenham Hotspur Stadium had largely remained a fortress, but Spurs' recipe for success on the road - or lack of - was not cooking up a treat. Conte made a brief return to the San Siro touchline to oversee a 1-0 loss to AC Milan in the first leg of their Champions League last-16 tie, but another period of rehabilitation followed for the Italian before his side were dumped out with a whimper courtesy of a goalless draw with the Rossoneri at home.
Only a few days beforehand, Sheffield United had ended Spurs' FA Cup run in the fifth round, as the wheels well and truly came off. Having thrown away a two-goal lead to draw 3-3 with Southampton, Conte mercilessly attacked his "selfish" players in a bewildering press conference, as well as appearing to point the finger at the owners for Spurs' trophyless streak, which now stands at 15 years.
It was clear that Conte's position was untenable, and the Italian was allowed to leave by mutual consent. His former right-hand man Stellini peculiarly stayed on to take the reins, but after 29 days, one win and a 6-1 obliteration at the hands of Newcastle United, he was gone too. Disdain towards Levy had hit new heights, and there were fleeting rumours of a takeover from Iranian-American billionaire Jahm Najafi, which were quickly dispelled by the Spurs chairman.
The under-fire chief hardly did himself any favours over the Fabio Paratici situation either - keeping the disgraced ex-Juventus sporting director on the books after his 30-month ban from Italian football was extended to a worldwide suspension - and he was allowed to resign of his own accord after failing with an appeal. Not for the first time, novice coach Ryan Mason was thrown into the deep end, and he was not helped by a season-ending hip injury to captain and number one Hugo Lloris.
The mood in North London briefly improved when Kane overtook Wayne Rooney in the PL's all-time charts with a 209th goal against Crystal Palace, but a subsequent 2-1 loss to Aston Villa - which prolonged their winless streak on the road to nine games - ended their wafer-thin hopes of Champions League qualification.
European football became further out of reach in a 3-1 loss to Brentford during their final home game - followed by an incredibly muted awards ceremony - and despite sending Leeds United down on the final day with a 4-1 drubbing, it was not sufficient to save Spurs' top-seven bacon.
PREMIER LEAGUE STATS
Wins: 18 (=6th)
Draws: 6 (=16th)
Losses: 14 (12th)
Goals scored: 70 (5th)
Goals conceded: 63 (6th)
Yellow cards: 75 (10th)
Red cards: 3 (=3rd)
Passes: 18,042 (7th)
Shots: 518 (7th)
Big chances missed: 43 (11th)
Saves: 111 (12th)
Tackles: 617 (13th)
Own goals: 1 (=12th)
Hit woodwork: 17 (5th)
Clearances: 725 (10th)
HOW DID IT COMPARE TO LAST SEASON?
Just like in the 2021-22 season, there were two managerial casualties in the white half of North London as Nuno Espirito Santo and Jose Mourinho lost their jobs, while Conte and Stellini suffered the same fate this time around.
Ceaseless opposition to Levy's ownership was also prevalent, and after forcing their way back into the Champions League last season, Tottenham's time with the big boys in the top four came to a swift end.
With a total of 60 points on the board, Tottenham finished four places worse off than the 2021-22 season - in which they amassed 72 points - but interestingly, they improved in the goals category, firing in 70 compared to 69 last term.
However, with the holes at the back not being plugged, Spurs lost 14 times - their most since suffering 15 defeats in 2008-09 - while conceding 63 goals, 23 more than last season and their second-worst tally in the Premier League since being breached 66 times in the inaugural 1992-93 campaign.
As COVID-19 cases reared their ugly heads all across Europe, Tottenham were memorably dumped out of the Europa Conference League by virtue of an awarded 3-0 win to Rennes, as their final group-stage game could not go ahead due to an outbreak in Conte's squad.
A last-16 elimination in the Champions League can therefore be seen as a significant improvement on the continental front, but the Lilywhites' domestic cup disappointment was prolonged yet again.
After losing to Middlesbrough in the fifth round of the 2021-22 FA Cup, Tottenham went out at the same stage to Sheffield United in 2022-23. Spurs also fell at the first hurdle in the EFL Cup to Nottingham Forest after getting as far as the semi-finals the previous year.
PLAYER OF THE SEASON: HARRY KANE
In amongst all the chaos that encompasses the Tottenham Hotspur Stadium boardroom and pitch, the Spurs faithful have enjoyed witnessing plenty of Kane's iconic celebrations throughout an unstable season - one which may prove to be his last in lily-white.
While Manchester City goal machine Erling Braut Haaland shattered records for fun en route to the Golden Boot, Kane was head and shoulders above everyone else in the race to be named the best of the rest, while also achieving plentiful individual glory in the process.
With 30 goals and three assists in the big time, the 29-year-old became the greatest scorer that his club and country has ever seen during the now-concluded campaign, surpassing Greaves for Tottenham while overtaking Rooney's record for England with a 54th strike in March's Euro 2024 qualifier with Italy.
A few more pages of history were written for Kane, who set a new record for the most games scored in during a Premier League season (26, overtaking Mohamed Salah's 24 during the 2017-18 season and equalling Andy Cole's 42-game season tally), breaking Sergio Aguero's record of the most goals scored for a single top-flight club, and becoming the first player to score 100 away goals in the competition.
Kane achieved all those feats amid a never-ending wave of stories over his future, and while his yearning for silverware could ultimately see him bid North London farewell this summer, the striker should no doubt depart having achieved legendary status.