As he lay in hospital after that injury at Turf Moor or worked through the summer on his rehabilitation, dare he have dreamed of such a renaissance in the last month or so?
Still only 21, Harry made his first start of the season five months down the line against Barnsley in the Carabao Cup and was then trusted by Mauricio Pochettino to start our testing Champions League match against APOEL in Nicosia, a 3-0 win.
He held onto his place for the impressive Premier League win at Huddersfield and then into the international break, where not only was he promoted from England Under-21s to the senior set-up, but earned his first cap and a start in the final World Cup qualifier in Lithuania.
On his return, the Academy graduate and Spurs fan from Hemel Hempstead was back in the 11 to face Bournemouth on Saturday and then the ultimate test, taking on Champions League holders Real Madrid in the Bernabeu.
Harry took on the challenge as he has all others, and relished every minute against Madrid’s midfield trio of Casemiro, Luka Modric and Toni Kroos, all starters when Los Blancos beat Juventus to become European champions for the 12th time in Cardiff in June.
His fearless display also summed up that of the team’s as we secured a valuable 1-1 draw to stay joint-top of the group and six points clear of both Borussia Dortmund and APOEL with three games to go.
It’s unlikely ‘Winksy’ even gave a second’s thought to those tougher times as he applauded our magnificent travelling support after the final whistle at the Bernabeu, but it was nice to be able to put his recovery into perspective afterwards.
“I guess it shows how far I’ve come since then,” said Harry. “That was a dark time so to come to a place like this, play as well as we did and get a result makes it all worthwhile.
“The manager has shown trust in me to start me in a game like this and that has given me real confidence.
“Every time he puts me out there I feel I have to repay him as well as all the coaches and all the players and I will always give my all. We were fantastic tonight and I'm delighted we came away with a point.
Below: Harry on the ball in the Bernabeu
“We played a slightly different game to what we normally play in the Premier League and we were excellent.
“We could have nicked it, they could have nicked it, we defended well, they defended well, we had good spells and they had good spells. It was a fairly balanced game. They had more possession but we had clear-cut chances as well.
“It's been a great couple of weeks for me on a personal level and this was a special night.”