The ex-Blues frontman, who starred at Stamford Bridge in his playing days, sees those in west London putting foundations in place for future success.
Frank Lampard is not under title pressure at Chelsea despite a big summer spend, says Jimmy Floyd Hasselbaink, with Jose Mourinho considered to face more expectation at Tottenham.
Two ambitious London rivals are set to lock horns in a derby date on Sunday.
Either could end the weekend at the top of the Premier League table after enjoying positive starts to the 2020-21 campaign.
Both are looking to ensure that they end the season within touching distance of the Premier League crown, with their respective squads being set up to compete for the grandest of prizes.
Chelsea are back in that pack after investing heavily in the last transfer window, while Mourinho now has his feet firmly under the table at Spurs.
Hasselbaink believes north London is demanding more than those in the west this term, however, with the former Blues striker seeing Lampard laying the foundations for long-term success.
He told Sky Sports: “As a squad, if [Tottenham] are not winning, or close to winning, the league this year then I think they will have underachieved.
“I think Chelsea doesn’t need to win it. Frank is not there yet. If they win it of course they will take it with two hands.
“But it’s only Frank’s second year, we all know what happened last year. He had to come in and let the youngsters play and he did magnificently.
“They have spent a lot of money but he is building for the future. In that aspect Spurs are a little bit further than Chelsea.”
The Dutchman added: “They are very close to each other at the moment.
“Spurs have got the strongest team, the strongest squad that they’ve had in the last 10 years, or the last few years.”
Lampard and Mourinho will have plenty of firepower at their disposal this weekend, with Chelsea welcoming United States international forward Christian Pulisic back into their plans, but Hasselbaink believes defences will be on top in a fixture that neither manager wants to lose.
He said: “It’s going to be very interesting, this match. It will be close and their will not be lots of goals.
“Mourinho will go and close the shop. But there’s something good going on at Spurs.”