Sixteen years have passed since Spurs supporters watched their side lift silverware, beating London rivals Chelsea 2-1 in the 2008 EFL Cup final at Wembley under former boss Juande Ramos.
Tottenham have since suffered defeat in four cup finals, three in the EFL Cup and one in the Champions League, while they also came up short in the 2016-17 Premier League title race as they finished second behind surprise champions Leicester City.
A number of high-profile names including Harry Redknapp, Mauricio Pochettino, Jose Mourinho and Antonio Conte all failed to win silverware in charge of Spurs, and Postecoglou is now the latest man tasked with ending the club's painful trophy drought.
If Spurs - who lost 1-0 at Crystal Palace in the Premier League last weekend - wish to progress deep into this season's EFL Cup, they must navigate their way past eight-time champions Man City when they lock horns in North London for a last-16 tie on Wednesday night.
McInerney: 'Spurs should aim to win EFL Cup'
McInerney has admitted that a much-changed Man City side could "crash out" of the EFL Cup in midweek and has explained why he is "not confident" ahead of their encounter with Spurs.
Having watched the Citizens enjoy plenty of success in the EFL Cup in recent years, with Pep Guardiola's side winning the competition five times between 2016 and 2021, McInerney believes that "success breeds success" and Spurs should push themselves to progress all the way in this season's competition, starting with a victory against 'one of the favourites' on Wednesday.
McInerney has also urged Postecoglou to not follow in the footsteps of former manager Pochettino, who 'prioritised' a top-four finish in the Premier League over winning a trophy during his time in North London.
Speaking to Sports Mole, McInerney said: "If I was Postecoglou, I would be aiming [to win the EFL Cup] because this is the kind of tournament Spurs could win given their attacking quality and the fact that they could knock out arguably the favourites, or one of them at very least. If I was him, I would go for it.
"I think success breeds success. I didn't really ever agree with Pochettino's priorities when he was at Spurs. I think he famously felt like top four was a trophy for them and he argued that it was sometimes more important.
Should Spurs prioritise trophy over top-four finish?
"I think if I was managing Spurs, I would absolutely be aiming for a trophy. That has to be the priority. If I was a Spurs fan, I would take sixth and a trophy over fourth this season.
"I know they might not agree, but that silverware is just so much more important than Champions League. I know the money's there (in that competition), but they're not going to win the Champions League. Maybe I'm wrong there, but just aim for a trophy and aim to put that curse you've had for such a long time to bed."
McInerney added: "There's also something nice about winning a trophy at the end of February or start of March. Winning the Carabao Cup is a really nice springboard for the end of the season because you get a taste of success.
"You have your big day out, you celebrate success, and then you have two more months of the season left and you're playing knowing that you can win something. I think that's quite empowering. I feel like Spurs should go for it.
"I hope City beat them, obviously. I just feel like City's priorities are lying elsewhere this season, especially given the size of the squad."
Meanwhile, McInerney has suggested that Guardiola will rotate his side on Wednesday and should rest star players including top scorer Erling Haaland, who netted twice in a 2-0 Premier League with at Tottenham in May last season.