He had already met Manchester United manager Tommy Docherty and expected to return to complete the deal when Docherty came back from holiday.
Instead, Rangers manager Willie Waddell called him to Glasgow Airport and told him he was going nowhere near Manchester.
“I’d already met Tommy Docherty at Manchester United beforehand, and he was going on holiday,” Conn told Football Presse.
“He said, ‘When I come back, we’ll get you down and get you signed.’
“I went, ‘That’s fine.’”
Then everything changed.
“This was in Glasgow before a Scotland-England match. I got a phone call from the Rangers manager, Willie Waddell, because they were going on a pre-season tour of Sweden.
“He said, ‘Meet me tomorrow morning at Glasgow Airport. You’re not going to Sweden.’
“And that was it.”
Conn was not given a detailed explanation. He simply boarded a plane.
“I hardly said a word. Even on the plane down, I’m going, ‘Why are we flying to London?’
“If I’m going to meet Tommy Docherty, it should be Manchester.”
Then Conn met Eddie Bailey, Nicholson's assistant.
“Bill Nicholson’s assistant was there, Eddie Bailey, and he came out with this Cockney accent.
“I went, ‘Oh right, something’s not right here.’”
Conn was beginning to work it out.
“It wasn’t until I got to Tottenham Hotspur Stadium — White Hart Lane — that I knew it was Spurs.”
The player Rangers had effectively taken out of one transfer and dropped into another was about to become Bill Nicholson's final signing as Tottenham manager.
And Conn was delighted.
“I wanted to play with Bill Nicholson. That was basically the whole story.”
Nicholson had already established himself as one of English football's great managers, having led Tottenham to the Double in 1960-61 and European success.
For Conn, the chance to work with him was worth taking.
Then Nicholson told him what Tottenham were prepared to pay.
“Once I met Bill Nicholson and he told me what my wages were going to be, before he got to tell me, I asked him for his pen so I could sign the contract there and then.
“You were getting three and four times as much as I was getting at Ibrox, with bonuses on top and what have you.”
The move had taken Conn from expecting Manchester United to unexpectedly arriving at White Hart Lane.
But there was another twist.
Nicholson resigned in September 1974, only months after signing Conn.
For the player, it meant losing the manager he had specifically wanted to work under almost immediately.
“I was his last signing,” Conn said.
Yet Nicholson did not simply disappear from Conn's life.
Even after leaving Tottenham, he continued to phone the player.
“Mr Nicholson used to phone me up and say, ‘Look, keep your head down, work hard, your turn will come.’”
Conn eventually got his opportunity.
“And it did.”
He became a popular figure at White Hart Lane, scoring a hat-trick against Newcastle United in January 1975 and helping Tottenham survive relegation that season.
But the move remains one of the strangest transfers of Conn's career precisely because of how little he knew about it.
He had expected Manchester. Rangers sent him to London. He expected to meet Docherty. Instead, Eddie Bailey's accent gave the game away.
And by the time Conn realised he was joining Tottenham, the decision was effectively made. Looking back, there was no disappointment about missing out on Manchester United.
“I wanted to play for Bill Nicholson,” Conn said.
That was enough to turn an unexpected flight to London into the beginning of one of the most memorable chapters of his career.
He had left Glasgow expecting Manchester.
He arrived in London not even knowing he was going to Tottenham.
And only when Eddie Bailey appeared with his unmistakable Cockney accent did Conn realise that Rangers had been keeping him in the dark.
“I went, ‘Oh right, something’s not right here.’”
It was football in another era: transfers arranged over the phone, players given few details and a young Rangers star discovering his new club only after landing in London.
“I didn’t know I was going to Tottenham.”
He certainly knew once he reached White Hart Lane.
Alfie Conn's book "What's it all About? The Alfie Conn Story" is from Pitch Publishing - which is available here.
