The Ibrox club posted a loss of £24million in their annual accounts for the year to June 2021, with their revenue slumping by 19 per cent amid the impact of the Covid-19 pandemic.
However, since then, Rangers have recouped almost £40million in transfer fees for the record sales of Nathan Patterson and Calvin Bassey, plus Joe Aribo, as well as securing a similar windfall from Champions League qualification, on the back of last season's lucrative run to the Europa League final.
Rangers are currently being monitored under UEFA's Financial Fair Play rules, which requires clubs to break even, but Bennett insists the financial situation is no longer causing him concern.
He told Rangers TV: "I've been asked how do we view the club's performance off the pitch in the last two and a half years.
"The most honest way of answering that on a personal level is that Rangers, ever since I was a kid, has given me sleepless nights because it's the team I love, and the team I love to see winning and hate to see losing.
"Up until very recently, the sleepless nights were not only about on the pitch. I lost a lot of sleep on off the pitch stuff at Rangers, the finances etc.
"Especially the end of 2019 going into 2020 and Covid etc. That was a particularly worrying time I felt. Not just for Rangers but for so many businesses.
"That was a time when many a sleepless night was had. I am now in a position that my sleepless nights about Rangers are about on the pitch. That's how it should be. That's a barometer of how far we've come, but it's also an honest asssessment of the fact that it's only recently have the four pillars been up, and it's working.
"Our player trading model if you look at it is months old. Not in the investment side of it, the development and investing in players has been years in the making, especially under Ross [Wilson]. Fully planned, fully intergated and joined up. We've sat through board meeting after board meeting, scrutinising and questioning that, as a board should do, and we're getting answers.
"Look at the player trading model. Two record transfers out of the club, but it only started in January of this year. That's why it's only recently that my sleepless nights have become virtually all about the football, and that's how I want it."
Bennet also addressed recent talk of a possible Ibrox takeover after American investor Kyle Fox pledged to invest £75million into the club over a five-year period if she is successful in acquiring a 25 per cent stake, which would make her the majority shareholder.
Discussions have not progressed though with Bennett expressing a “never again” message over the lessons to be learned from the Craig Whyte era which resulted in the club suffering liquidation in 2012 and reentering at the bottom of the SPFL.
"It's not unusual for this football club, and perhaps other football clubs, to be approached by potential investors," Bennett added.
"Some of those come to fruition, some of those have come to fruition. Stuart Gibson came to us and that worked, John Halstead came to us and that worked for both parties. They were both perfectly supportive investors in the club and with that in the board room, and outside the board room. I've talked in the past about George Letham, George Taylor was outside the board room and is now in the board room. But others, we have terrifically supportive investors.
"Don't take my word for it, just look at the facts. They went to the well time and time again to invest major investment on the pitch and off the pitch. There has been speculation about the American group in particular recently. They are one of a number of groups or individuals who have come and spoke to us, and I believe that will continue to happen.
"The bit that surprised me, when I was in Amsterdam the noise seemed to go up about potential sellers from within the board room. I think I know Douglas Park as well as anyone can know Douglas Park. I consider him a friend as well as the chairman of this football club. Douglas isn't a seller, I'm not a seller. In fact, I have recently increased my position above five per cent. And when this said American group did approach us, I actually took that as an opportunity to sound out our big investors and ask 'where are you, what do you think of this?'
"They rightly said there is no harm in listening, and we do listen to a lot of proposals and that will happen again, I'm quite sure. There is no harm in listening, especially from a fiduciary point of view. We gave quite a lot of time to that situation. But what was very interesting was from John Halstead, to Julian Wolhardt, to people outside the boardroom and in the boardroom there was no interest in selling.
"Now, I'm also struck by the phrase never again in this context. The phrase never again was used at the time of regime change in 2015, and never again can mean perhaps different things to different people. What I'm trying to get across is this is a board that really believes in never again, in terms of one individual or one party calling the shots and owning the club. This is my view, and I know it's a view shared by our current board.
"The ownership of Rangers Football Club should rest on a number of shoulders. You know what can happen when one entity walks away. People can get board, people's lifestyles can change, people's life can change. If it's resting on one set of shoulders things can change. When you have a number of sets of shoulders carrying the load you are not beholden to one individual walking away, or something could befall that individual. That is what never again means to me and my colleagues."