Turn the clock back two years and the Dutch favourite was back where he always loved to be - playing in goal for us as emergency cover for Ian Walker and Espen Baardsen.
The goalkeeping coach had to dust off his competitive gloves as we hit a crisis back in September 1998. Ian Walker was injured, Espen Baardsen was ill and Segers, then 38, was called upon by caretaker boss David Pleat for the Premiership trip to Southampton and the visit to the Lane of Brentford in the second round, second leg of the Worthington Cup.
Segers won rave reviews after a fine display at The Dell and played his part as we overcame an early shock to beat Brentford 3-2 and progress to the third round.
Baardsen was soon recalled after recovering from illness and that cup tie against the Bees remains Segers' last competitive match.
So naturally the arrival of the same club at the same stage of the same competition had the former PSV Eindhoven, Wimbledon and Wolves stopper delving into his memory banks.
He recalled: "When I signed for Tottenham it was as cover for Ian and Espen and the other side of my job was the coaching of the goalkeepers.
"By signing my contract I already knew that on a long-term basis I was going to be the coach and I accepted that my playing days were over. So to get two extra games was a bonus for me.
"I can remember the game against Brentford. We had an early scare when they scored and we looked at each other and thought 'what's going on here' but I think we went 3-1 up before they scored again at the end.
"We did a very professional job and didn't panic at 1-0 down. At the end of the day we are in the Premier League and should beat these clubs but when it is 1-0 or 1-1 they still have hope.
"So for Tuesday the boys have to be very professional. If you get into the next round you can soon progress, get to the final, win it and then you are in Europe."
Turn the clock forward to the present day and Segers loves his job as goalkeeping coach to Neil Sullivan and Walker.
But did he miss playing? "Of course I do. I'm a goalkeeper, I'm a player and you want to play as long as possible but sometimes you have to tell yourself that it is time for the youngsters coming through.
"I have accepted that my playing career is over and I've moved to the next step. It is like a new career for me being a goalkeeping coach and I really enjoy it - we have two great goalkeepers at the club."
To listen to Hans Segers' thoughts, click here
The visit of Brentford to White Hart Lane stirs poignant memories for Han Segers.