It was season 2000-01 when 'Doc' scored the late winner in the third round tie at Leyton Orient and a similarly tricky first obstacle lies ahead this Saturday with another London Derby against Crystal Palace.
Gary's header at Brisbane Road was his second goal in two games after being drafted into the side in central defence in the previous game against Newcastle United at the Lane. Memorable cup ties against Charlton, Stockport and West Ham then followed before the class of 2001 bowed out at the semi-final stage against Arsenal.
"It seems like an eternity ago now! We ended up having a good cup run and got to the semis, it went really well for me," reflected Gary, who has much less fond memories of last season's early exit at St Mary's where he was a second half substitute. "It was bad last year losing to Southampton and that was probably the lowest point - it really was a hammer blow for us.
"The semi-final year did launch my career here, definitely. I broke in the week before against Newcastle - my home debut - and I scored. Things took off from there until the leg break and I haven't had five or six games together to really get my form back. Hopefully I can do that in the long run."
Gary hopes that Cup progress can spark our season back into life on Saturday but knows the pressure is on and Palace - under the changed managerial guard of Iain Dowie - will fancy their chances of an upset.
"We'll keep our heads up now, we have the Palace game and we are usually quite good in the cups. Hopefully we'll get on a good run and keep the spirits up.
"We've a lot to lose on Saturday. They are going to come here and not really be expected to get a result. They will look at our recent results and think now is the best time to try and get one and we have got to be big enough to take it on board and make sure we get the result.
"We've got to be positive and have faith in our own ability. They will show passion and we have to match that."
Gary Doherty well remembers the FA Cup run that effectively launched his career as a Spurs player.