The bombshell dropped on the Matsatsantsa hierarchy late last month following confirmation that the Botswana international would move on when his contract expired, and the Glamour Boys rubbed salt in the wound by making an announcement.
Matthews says they couldn’t afford to keep Ditlhokwe.
"I can count on one hand the amount of players I've lost on a free transfer in my 23 years at the club. I'm obviously very sad to have lost TT because we found him from nowhere in Botswana.
We gave him a platform to showcase his talents, unfortunately, business is business and, the financial requirements from his side over the past three, or four months, we've tried to find a way to keep him to extend him, and offer all sorts of creative ways of how he can get out of the club, whether it was overseas, or locally and push the numbers as high as we could go", Matthews claimed.
Speaking to SABC Sport after the club had confirmed iKhokha as a new sleeve sponsor, Matthews suggested a contract extension for the Botswana captain would have crippled the club if it went ahead.
"It got to a point where my CFO said to me, 'sorry Stan, we can't go beyond that and have a financially sustainable club moving forward, we can't create an artificial economy where it doesn't make financial sense to be paying a player beyond a certain level'.
So that was very sad for me because I would never have wanted to lose TT", he said.
"If his representatives had been more forthright with me, candid with me, early on that he was having multiple discussions with people, then perhaps I would've taken a different view and sold TT in July so that I could reinvest the money.
So I did feel a little bit let down by the process because we were always upfront and open about where we were. Even myself, with TT to say 'I can't go to certain numbers, but I can do other things for you and I can give you an exit clause and I can do other things for you'.
So I did try my best as CEO, to give him a carrot, to stay at the club and also to have an out when a good offer came his way, but it didn't work out. I can't cry about it because the majority of the players that I've brought to this club have been free agents and pre-contracted players. So you live by the sword, that's how it works", Matthews conceded.
There were talks behind the scenes that Ditlhokwe could leave SuperSport early to move to Naturena, but with the transfer window now closed he is staying until the end of June.