McKenna joined Spurs as a teenage midfielder, became reserve team captain and was on the fringes of the first team squad before a chronic groin/hip issue forced him to give up playing at the age of 22.
Alex Inglethorpe (now academy director at Liverpool) and John McDermott (now technical director at The FA) took McKenna under their wing though and helped the young Northern Irishman quickly grow as a coach.
"I first went there at 14 years old on the plane from Ireland with three other young footballers. After travelling back and forth for a while, I moved over when I had just turned 16," recalls McKenna, who takes his Ipswich to Spurs for a Premier League clash on Sunday.
“There were some nice moments in and around the first team. I scored a good back post header in pre-season. That was Dimitar Berbatov’s first game in English football and I got us the winner out in Bordeaux. It’s sad in some ways that that’s the highlight! Playing at Celtic Park was a big one, at 18, under Jacques Santini. Playing at a massive stadium against a club that I had an affiliation with was a pretty special one.
"Of course there was disappointment with the injury, but I was well looked after by the club after that and will always be appreciative of that."
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He continued: “I had a second major hip operation on top of some other little operations around the area. I went into it knowing that it was pretty much make or break, when I came around from the anaesthetic the surgeon said it was ‘break’, so from there I quickly reassessed.
"I went straight from that surgery to coaching on crutches within a few days. That was a group that included Harry Kane, Andros Townsend, Ryan Mason, Steven Caulker, Adam Smith, John Bostock and probably four or five others I’m doing a disservice to who have gone on to have very good careers.
“I was 22, they were 17/18. I’d played with a large majority of them in the reserve side. I’d captained a lot of them. They were great with me. You can tell with the careers that so many of them went on to have that it was a pretty special group. They were a privilege to be around.
“I went to an international youth tournament where we played against Barcelona and Sporting Lisbon. I remember that trip like it was yesterday. That first access to top level coaching, top level players and top level European methodologies got me absolutely hooked and was a big part of me getting the bug that I’ve still got today.
"I was certainly blessed to make my first steps as a coach at Tottenham because, at that time, I would say they were country leaders in terms of how they developed players. The first environment that you have coaching experience in is huge. For me the first exposure you have to coaching has a bigger affect than any coaching courses. I was very lucky with the quality of people that set me on the right path. It’s a club I’ve got great fondness for."
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McKenna went on to become Tottenham U18s manager before taking on the same role at Manchester United and rising to the position of assistant first team manager, working alongside Jose Mourinho, Ole Gunner Solskjaer and Ralf Rangnick He left Old Trafford to become first team boss of then League One club Ipswich Town in December 2022 and quickly oversaw back-to-back promotions into the Premier League.
On the first team managers that were at Tottenham during his time there as a player and coach, McKenna said: "There was David Pleat, Glenn Hoddle, Jacques Santini, Martin Jol, Juande Ramos, Harry Redknapp, Tim Sherwood, Andre Villas-Boas and Mauricio Pochettino – so quite an eclectic mix!
“I was injured during the whole time of Harry’s time at the club, I might have trained once in between the two surgeries, but everyone knows what a positive character he is. He put his arm around me a couple of times and told me how good a player he thought I was, when he probably hadn’t seen me play! That’s Harry, he’s trying to make me feel better!"
Asked if he would have liked to play in the current Tottenham side, the Blues boss joked: “No, I wouldn’t have been fast enough! I would have had the engine for it, but I definitely wouldn’t have been fast enough! I don't think I'd have got picked too much."