As both a player and manager he experienced many highs and lows over four decades of involvement at the sharp end of the sport.
Relegation and promotion, FA Cup success and despair, League Cup joy, international caps with Scotland, being hired...and fired...as manager by some of the biggest clubs in the country – there is not much that The Doc has not experienced.
However, there is one glaring omission on his CV – not once was he crowned a champion of England – although he came mighty close to achieving the feat on several occasions.
None more so than during the 1952/53 season when he starred alongside the legendary Sir Tom Finney as Preston North End finished runners-up in the old First Division – pipped to the title by Arsenal courtesy of having an inferior goal average.
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In the days of two points for a win, the title rivals had ended the season locked on 52 points after 42 games.
But unfortunately for Docherty and his PNE team-mates, it will be the Gunners who will forever be known as the champions that year thanks to the narrowest of margins.
Goal average was the preferred option used to differentiate between teams who had finished on the same number of points until it was abolished in favour of goal difference in 1976.
Calculated by dividing goals scored by goals conceded, Arsenal edged North End by an average of just 0.099.
Indeed, a five-goal swing over the course of the season would have seen PNE crowned champions instead of the North Londoners, who clinched the championship by defeating Burnley 3-2 at Highbury – two days after North End had beaten Derby County 1-0 at the Baseball Ground .
“I remember waiting for the result at Burnley,” Docherty recalled. “It was very disappointing when the result came through because anything other than a win for Arsenal would have seen us win the league.
“Then you think if only we’d have scored another couple of goals or not conceded that many against so-and-so then we would have been champions of England.”
A virtual ever-present during that campaign, Docherty was also a stalwart of the teams which finished third in 1957 and second to Wolves a year later.
In a further hard luck tale, North End also reached the FA Cup final at Wembley during that era, losing the 1954 showpiece 3-2 to West Bromwich Albion.
With his 89th birthday fast approaching later this month, Docherty still casts a rueful smile when he contemplates how close that PNE team came to greatness.
Even now the names of many of his team-mates from the 50s still slip effortlessly off his tongue.
“Else, Cunningham, Walton, Marston, Morrison, Forbes, Finney, Foster, Wayman, Baxter...we had a great side,” he said.
“And we played great football which was good to watch.
“The team picked itself every week.
“It wasn’t like there was a player pool or a big squad.
“I remember when we played Arsenal or Tottenham down in London, we would meet after training as a team on the Friday at Preston train station. There would be just 12 of us on the platform and we would travel down to London together.
“On the Friday night, we would go to the Palladium and see a show, then go back to the hotel and have something to eat.
“Then it would be off to bed to get ready for the game the following day.
“North End back then were one of the top clubs in the country.
“The gates used to prove that. We would be getting 35 to 40,000 every home game.
“When I see the continentals play today – I think they call it tiki-taka – that’s the way we used to play.
“It would be two-touch football – control-pass, control-pass.
“Although when Sir Tom used to get the ball, he would either pass it or go and take three players on and score a goal!”
Such is Docherty’s affection for Finney, North End’s loss in the 1954 FA Cup final was doubly disappointing as it prevented PNE’s greatest ever player from adding a further layer of history to his legacy.
“Stan Matthews had done a big thing for Blackpool the year before when they beat Bolton at Wembley,” Docherty said.
“That final is always remembered as the Stanley Matthews Cup Final.
“So when we got there the next year, we were hoping it was going to be the Tom Finney Cup Final.
“But by his standards, Tom had a poor game.
“Whether he was injured or not I don’t know, although he would never have mentioned if he was – he would have just gone out and done his best.
“I think I gave a penalty away for West Brom’s second goal, which didn’t help matters,” said Docherty, who is the last surviving member of the ’54 final from either side.
After more than 300 games for Preston in a nine-year stay, Docherty departed for Arsenal in the summer of 1958.
His departure still leaves a slightly bitter taste in his mouth even now.
Planning ahead for the end of his playing days, Docherty was hoping to purchase the post office in Lowthorpe Road.
With a benefit year due in the not-too-distant future, he asked the club for £300 as a deposit for the business.
However, his request was turned down and it led to his £30,000 transfer to the Gunners.
“Ron Greenwood was the assistant manager at Arsenal and he had heard that I had asked for a transfer,” Docherty said.
“He asked me if I fancied going to Arsenal.?
“Of course it went all the way up to the start of the season and I found myself in the office of Preston manager Cliff Britton at quarter-to- two on Saturday afternoon.
“We were playing Arsenal that day at Deepdale and Cliff said to me, ‘Do you want to play today or do you want to go to Arsenal?’ – I said, ‘If you can’t help me with a down-payment of £300 for the shop, then you can’t think much of me’.
“It broke my heart to leave Preston.”
Docherty had another title near miss when he moved to Highbury – the Gunners finished third in his first season.
He retired from playing in the early 1960s and went on to manage a whole of host of clubs, most notably Chelsea and Manchester United.
He blotted his copybook slightly in the eyes of North Enders when he returned to Deepdale in 1981 for an ill-fated stint as manager.
“The old adage goes, ‘You should never go back to your old club’.
“They always say it never works out and in my case that was true.
“It never worked out for me because the club had no money to buy in any quality players. Preston were already on a bad run before I came and it didn’t help matters that the results were poor.
“It will never change the affection that I have for the club.”