Gilbert was the first coach to take the Highlanders into the playoffs.
He was also one of the first players to ever play a game of rugby at Molyneux Park.
About 50 years later, Gilbert will be sideline as the first professional game is played at Molyneux Park when the Highlanders host the Waratahs in a pre-season match on February 1.
Gilbert, who coached the Highlanders to the playoffs in 1998 and to the final a year later, said he always wanted the Highlanders to play in Alexandra when he was heavily involved with the franchise but it never eventuated.
He had spent a lot of time in Alexandra and although he is now based in Dunedin, he had a real affinity for the town.
Gilbert (75) taught in the town in the 1960s and his children were all born there.
''I played for the Alexandra club for quite a while. Those were the days when we played at Pioneer Park ... at that time we did not have a club rooms. So we just changed in the pavilion and the after-match was down at the pub,'' he said.
''Molyneux Park was being developed. It was all lupins to start with up there, but through a lot of work by a lot of people the ground came about. It was all voluntary work. I remember shovelling a whole lot of sheep poo - a lot of us did - to raise funds to build the club rooms.''
The park became a rugby field in the late 1960s and the first game was played between the Alexandra club and a group of Ministry of Works workers who were building power pylons in the area.
''Everyone was pretty keen to play the first game. I remember at the start of the game we had an agreement where we would score a try - so Gordon Whyte scored a try for us - and then they scored a try, and we then got on with the game.''
Gilbert, who was a loose forward in his playing days, said the game might have been about 50 years ago, but time had gone fast.
Gilbert describes himself as a museum exhibit these days with the Highlanders. He gets along to most training, attends meetings and talks to the coaches.
He was brought into the organisation in 2014 as a form of mentor for the coaches and he still pokes his nose in.
He said the players in the Highlanders might come from all over New Zealand these days, but communities such as Alexandra were important for the Highlanders.
''They may be small communities but they play a big part in the Highlanders. The hinterland - the likes of Maniototo, central, south and west Otago.
''The game has changed a lot but good players are still good players. Good teams are still good teams. The methods and trainings are far more advanced than what we had when we were still coming through from the amateur days.
''Players are way more professional these days, even the new boys coming through. But you can only sing with the choir you have got.''