Jamie Redknapp says Tottenham are still paying for the mistakes in the transfer market a year ago.
He insists Mauricio Pochettino's side are too far behind Arsenal in terms of quality and structure to finish above them this season.
He told SkySports: "A few seasons ago Tottenham had closed the gap on Arsenal – but now they’re further away than they have been in a long time.
"Spurs are miles away from being a top four team now and that’s down to their transfer policy. Spurs need to re-think their structure and how they sign players.
"For instance, they sold Gareth Bale and haven’t replaced him with a left-sided player; they’ve got Erik Lamela, Andros Townsend and Aaron Lennon who all want to play on the right."
Redknapp is however basing his comments on a sample size of last season, and five games this campaign.
Last year Arsenal beat Spurs three times, not even conceding a goal, and finished comfortably above them in the table.
To a degree he is right, with Arsenal aiming to win the title this season, and Tottenham aiming simply to finish in the top four.
They are certainly expected to finish higher this season, for Mauricio Pochettino to topple them in his first season would be a surprise, considering no other Spurs boss has achieved this during Arsene Wenger's tenure.
In time however, the Argentine is determined to change this, insisting he wants a legacy as lasting as Wenger's at Arsenal, and as his time at the club progresses, he will have more of his own chances to bring in his own players to suit his style and achieve results.
Tottenham's players have a chance this weekend to show him that major upgrades are not required.