Tottenham are a club close to both Lipton's heart and professional life, and attention turned to the Dubliner's form this season.
Matt Doherty at Spurs
While the playing staff have hardly covered themselves in glory, it may be the case that Doherty's career at the club may be over before it sputtered to life.
"I wouldn't be surprised if there wasn't a second season for him at White Hart Lane," Lipton said of Doherty's plight.
"I think that if they could get even two-thirds of their money back they probably would [sell him.] It hasn't worked, for whatever reason it simply hasn't worked. Doherty would admit that.
"It has not been a disaster but it has not been a million miles short of that. He has failed to get into the team and they have ended up picking [Japhet] Tanganga ahead of him at right-back and he's a centre-half.
"He has just not done it."
What is behind the malaise?
"I thought from day one he didn't look right. That opening game of the season, he was disappointing. He seemed to be a player lacking conviction and self-belief.
"The player they thought they were buying was an attacking full-back-stroke-wing-back who would hurt teams and it simply didn't happen. How many goals has he been responsible for? How many assists? Far too few.
"They way they were playing, the full-backs were critical members of the team in an attacking sense. Unfortunately, Doherty wasn't a critical member of the team in either an attacking or a defensive sense."
While he believes the situation to be salvageable, Lipton believes Doherty could be looking at consecutive off-seasons of change.
"He doesn't seem to be able, this season at least, to be able to cope with the burden of expectation. I'm not saying that it's beyond him, there are plenty of players that have struggled in years one and two, and then come back in years three and four.
"It isn't inconceivable, but at the moment I would absolutely not be shocked if he was sold this summer."