The former executive chairman, who left the club in September after almost 25 years, was speaking to reporters at Windsor Castle on Wednesday, where he was made a Commander of the Order of the British Empire by the Prince of Wales for services to charity and the community in Tottenham.
Asked how he felt watching Spurs from the outside as they sit just two points above the bottom three with two games remaining, Levy was candid.
"Emptiness. But I'm optimistic that we will remain in the Premier League."
"It's been very, very difficult — Spurs is in my blood. I could never have envisioned this at the beginning of the season."
"Obviously incredibly disappointed. Let's look forward and very much hope that next season we're still in the Premier League."
He was equally direct on whether the signs were there during his tenure.
"Never, no, not in a million years."
Levy added that relegation was not something the club ever considered when committing to the £1 billion redevelopment of their stadium in 2019 — a project that defined the latter part of his chairmanship and drew sustained criticism from supporters who felt commercial ambitions took precedence over the squad.
Spurs were held to a draw at home to Leeds United on Monday night, which means West Ham United remain in contention. If the Hammers beat Newcastle United this weekend, Tottenham will enter the drop zone ahead of what is already an ominous assignment — a trip to Stamford Bridge to face Chelsea, a ground where they have won just once in the league in the past 36 years.
"Always tough, never a good place for us," Levy said. "Hopefully this year is going to be different."
Head coach Roberto De Zerbi, appointed earlier this season, has steadied the ship — Spurs have taken eight points from their last four matches. A final-day home fixture against Everton follows the Chelsea trip.
Levy acknowledged the scale of what he had hoped to achieve during his time in charge.
"What I would have hoped for is winning the Premier League, winning the Champions League — easier said than done."
On whether West Ham's controversial defeat to Arsenal had given Spurs a reprieve, he kept his focus narrow.
"It's interesting getting into individual games but all I'm focused on is making sure Tottenham stay in the Premier League."
He also revealed a brief exchange with Prince William — a lifelong Aston Villa supporter — when he received his honour.
"I thanked him for allowing us to beat Aston Villa when we played them a few weeks ago. He wished us luck the rest of the season, very much hoping that Tottenham survive in the Premier League."
Levy confirmed he still watches every Spurs game. "I'm always optimistic. I pray every day that we will survive."