Despite being feted as teams on the rise, Tottenham and Liverpool have yet to win a single trophy under their current managers.
Pochettino has been in charge at Tottenham since 2014, while Klopp is in his third season with Liverpool, making the forthcoming campaign a watershed moment for both bosses.
After finishing third in the Premier League in 2015 and second last season, Tottenham suddenly find themselves in danger of being stuck in reverse at a time when they should be putting their foot on the gas.
Building his team around England stars Harry Kane and Dele Alli and, with Christian Eriksen, Toby Alderweireld, Jan Vertonghen and Son Heung-Min all influential in their own right, Pochettino has assembled a group capable of beating any side in the country on their day.
But the 45-year-old Argentine and his players have come up short two years in a row as the pressure of the title race proved too much for them.
Last season, they had Chelsea in their sights in the closing weeks before an FA Cup semi-final loss to the Blues triggered a stumble that saw them finish seven points behind the champions.
Making up a deficit of that order won't be easy this season as Tottenham have the thorny issue of playing their home games at Wembley while White Hart Lane is being redeveloped.
Wembley wasn't a welcoming arena for Tottenham when they played their European fixtures there last season, prompting claims that the high tempo pressing game Pochettino prefers was ill suited to the English national stadium's large pitch.
Adding to Pochettino's discomfort, he has so far gone through the summer transfer window without making a single signing.
While Tottenham's title rivals have shattered records with their lavish spending, Pochettino heads into the new campaign with a weaker squad than last year after selling England right-back Kyle Walker to Manchester City.
- Limited success -
Publicly, Pochettino backs chairman Daniel Levy's cautious approach in an historically expensive market.
Yet the former Southampton coach might not be so sanguine if the window closes without fresh faces finally arriving in north London.
"We are working, trying to add some players to the squad," he said.
"Our idea was, the same as before, to try to provide the team with more strength and try to sign a few players before the end of the transfer window."
At Anfield, Klopp has spent the summer trying to close the gap on Tottenham and the rest of the Premier League's big guns with only limited success.
The German splashed out a club record £43.9 million ($57 million) on Roma winger Mohamed Salah and added Hull defender Andrew Robertson to the mix.
But Robertson is unlikely to be a game changer, while Salah's last taste of the Premier League with Chelsea was utterly forgettable.
Klopp has also failed to land Southampton defender Virgil Van Dijk and Leipzig midfielder Naby Keita, while having to fend off Barcelona's attempts to sign Reds playmaker Philippe Coutinho.
"Until the 31st of August we run through the world with open eyes," Klopp said of his transfer problems.
"It's not that we decide on our own, it's also about other clubs."
Having enjoyed unprecedented success with Borussia Dortmund, Klopp has proved he can beat the odds before, but winning Liverpool's first title since 1990 would be the 50-year-old's finest achievement.