Last season was the most successful season of the 29-year-old's career, yet he made no attempt to hide his desire to leave Craven Cottage. With less than a year left on his contract, Fulham eventually sold Dempsey to Tottenham on transfer deadline day after a period of speculation that unsettled the midfielder. This week Dempsey intimated he could have stayed had he felt more "valued and appreciated", but Jol laughed off those comments ahead of his return to west London.
"We did everything we could do so there are no regrets," Jol said.
"He wanted to be appreciated financially and he wanted a bigger club, a Champions League club, and that is what he probably got with Spurs.
"He didn't feel appreciated financially, but I am not the one deciding over the contracts.
"He said it time after time again that he wanted to go to a Champions League club.
"Even when I said in my last conversation with him that I loved him, it was not good enough to keep him here."
Asked if there was anything Fulham could have done to get make him stay, Jol shook his head and said: "No, no.
"You know what he wanted. He wanted to go to a Champions League club.
"If you feel appreciated, you would like maybe to stay at Fulham so there is a contradiction there.
"I think he felt loved but he still wanted to move, but of course I understand what he means.
"From the first day he came back from holiday he didn't want to play here. He wanted to move so of course you can force the issue and then come up with things.
"But hopefully he will get over it and hopefully he will feel loved at Spurs."
Dempsey will not be the only player making his first Fulham return on Saturday, with Mousa Dembele also set to feature after also leaving the club for Spurs during the summer. The Belgium international parted on far better terms, but Jol expects both players to receive the same reception from home fans.
"I feel that Dembele was very popular and Clint Dempsey was very popular as well so I think it is okay," Jol said.
As if there was not enough to spice up Saturday's encounter, the match also sees Jol and striker Dimitar Berbatov come up against their old club.
"You get used to it," Jol said about facing Spurs.
"We played them last year so that was a different experience and was nice.
"For us, of course, it just another game, a home game. We need the points and the same applies to them.
"We are quite excited because they have terrific players and we've got some good players.
"We had a decent result at Chelsea so for us the game is not about Spurs, it is about trying to get the three points."
Jol left an indelible mark at Spurs, with Gareth Bale, Aaron Lennon and Tom Huddlestone among those to arrive during his time there. The Dutchman also brought Darren Bent to White Hart Lane and would not rule out a January move for the out-of-favour Aston Villa striker.
"You never know but we have three good strikers," he said. "We have Hugo Rodallega, Mladen Petric and Berbatov, then in the hole we have Bryan Ruiz.
"We could do with maybe another creative player in that position, then I could leave Berbatov up front all the time.
"As the situation is now, it is different, but you never know what will happen and what will change.
"If you saw him at Charlton he scored almost one in two games. I thought he was a quality finisher."