The six years Strachan spent with the Whites after Howard Wilkinson paid Manchester United £200,000 for him in 1989 proved to be the turning point for the Yorkshire club.
After leading Leeds to the old Division Two title in his first season before following up a fourth place finish with a glorious championship winning campaign in 1992, Strachan remains loved by the Leeds supporters.
There will be 5,000 travelling fans inside the Riverside Stadium today, when Strachan could receive a better reception from the away fans than he does from those of a Teesside persuasion if Boro fail to perform.
A smile still rises across Strachan's face when he recalls his time at Leeds, which must seem a million miles away from his current predicament of trying to lift Boro out of the doldrums.
I lived in a different world from anyone else that was in the league at that time a Leeds world where everywhere you went the grounds were full and every game was a cup tie, said Strachan.
There was some great football going on. It was hard but the game is better now because the back-pass rule was not in there and that rule has helped the game become far better. It was a rough league but then Howard changed it again.
It is a different game now.
There were ways you could take short-cuts and get results.
Howard was a very clever man. But because he hasn't got a PR or media man behind him, or he doesn't know how to use the press, he hasn't got a job and there are people who couldn't lace his boots who are working.
Strachan has constantly insisted he never uses the Leeds model, or any of the clubs he has played for in the past, as the one to replicate.
Trying to pick up different ideas and aspects along the way has always been his way of doing things.
But, even with that in mind, the 53-year-old would love to have a team similar to the one which delivered promotion back to the top tier of English football in 1990, which was the only season of his playing days he spent in that division.
The Championship, out of which he now finds himself trying to lead Boro, has changed in the succeeding decades, but Strachan would still love to have a team of similar ilk at his disposal.
That Leeds team was so successful because it was full of characters.
It had a great manager and the players themselves wanted to work very hard,
said Strachan, who has tried hard to bring in characters capable of delivering promotion at Boro.
It was a magnificent journey to be on. I remember I used to play in a midfield with Chris Kamara, David Batty and Vinnie Jones.
Howard came in at half-time and said when are you going to start tackling.' I said are you taking the Mick - what about these three'
It was a terrific time and when you bump into people and they say that was great fun it is fantastic.
After a fortnight in which Strachan has been forced to explain the comments for which he was criticised in his post-match interview following the 2-2 draw with Portsmouth, he recalled that his Leeds team-mates used to feel the wrath of his tongue on a regular basis including Jones.
It was certainly an interesting experience to play alongside Vinnie, said Strachan. Vinnie did mention a couple of times that he wasn't going to take me on verbally.
But I did have a word with him every now and again because he was going to get himself sent off and I said listen I'm not having it.
If you get sent off, that means I'll have to run more and if you clap the fans when you go off, and kiss and shake everyone when we're down to ten men, well it's not on'.
I told him to get his act sorted out and he was brilliant. I think he was only booked once all that season.
He was a great trainer and great person about the place, that's what dressing rooms need.