Doc made his first start of the season in a striking role in the 30th December fixture alongside Willem Korsten. It was not memorable for the right reasons, but it did signal a turning point in the Irishman's Spurs career.
"That was probably the worst performance I've given and I think, as a team performance, we didn't play anywhere near what we could," recalled Gary of the miserable 3-0 defeat.
"It was on telly as well and it was just a bad game for us - everything about it was horrible!"
Three days later Gary remained in the side that took on Newcastle at the Lane and George Graham switched him to the central defensive role that he is now known for. He scored with a bullet header, hit the post and totally looked the part at centre-half.
"Then...," smiled Gary. "Luckily enough, the gaffer kept faith with me for the Tuesday game at centre half and things went on for me from there and went well.
"I went on a little run from there with goals from centre half. It's strange, I couldn't score when I played up front, but from centre half I got a couple of goals."
On the defeat at Portman Road, Gary suggests that it was one of those nothing goes right results that happen from time to time, but he does not foresee a repeat.
"You get those games. It was a strange time for the club, we had a lot of injuries and things like that. With them being bottom of the league now and us flying I can only see three points for us on Saturday.
"It was always going to be hard for them, they've lost Marcus Stewart for a while too. They always say the second season is harder, but I really didn't think they'd struggle this much and I think they're in a false position at the moment."
Gary Doherty has good reason to remember last season's away encounter with Ipswich at Portman Road.