Sheppard grew up in the UK and came up against a young Kane when he was coming through the Leyton Orient academy. The 25-year-old then trained with Kane in 2011 when the Tottenham striker joined Orient for six months on loan.
Kane was only a teenager at the time, and yet to become a Premier League superstar and captain of the England national team, but the Spurs marksman still made a big impact on the teenage Newcastle attacker.
“He came on loan, him and Tommy Carroll,” Sheppard told The World Game.
“I always remember Harry Kane’s youth team manager was watching him play and he was sitting with my youth team manager.
“And Harry Kane’s said to mine ‘Harry Kane will play in the Premier League and score lots of goals’. And that was on when he was on loan at Leyton Orient.
“When you looked at him back in the day he wasn’t as stocky as he is now. But he could still score goals and he was strong.
“You could see he had that eye for goal and his mentality just to keep going and pushing himself as well. I played against him a few times when he was with the Tottenham reserves, but seeing him in training every day is different as well.
“Just seeing how hard he works. He had a few different loan spells, some of them worked well, some of them didn’t but he’s a very strong character and someone I look up to to push myself forward as well.
“Just seeing him in training, seeing his work ethic was a big thing.”
Sheppard’s career path saw him eventually released by the O’s in 2012 and spend several seasons playing in England’s unforgiving National League for the likes of Braintree Town, St Albans City and Histon.
“It was a great experience,” he remembers.
“I was a 17-year-old, 18-year-old boy just getting bashed around by grown men who just didn’t care. You had to grow up vey quickly and get used to it or you wouldn’t last very long.
“Luckily for me I deal with it pretty well and learned from that experience.”
In 2014 the striker decided to take the plunge and move to Australia, joining NPL Victoria club Heidelberg United. After impressing with the Bergers, where he banged in 24 goals in 49 appearances, he had brief spell with Avondale before joining Finnish club SJK.
The Jets then handed Sheppard a trial in 2018 and he signed with the A-League club. Last season he scored three goals in 22 games.
Sheppard admits it has been a hard journey but one he is grateful for.
“I’ll be honest there has been a few times where I’ve considered should I keep playing,” he said.
“I know a lot of people have that. But I just couldn’t give it up. I had to realize and think about what was it was that I really needed to work on to improve to get me to that next level, which I think I’ve done.
“Obviously I need to do it a lot more to keep on improving and progressing, but to get me to this stage in my career I definitely learned a lot and the experiences I’ve had along the way, a lot of my friends back in England they started off at academies that maybe were a bit higher up than what I was playing, but the experiences I’ve gained I wouldn’t change it.
“It’s made me who I am today.”
Sheppard, who is currently sidelined for Newcastle with a foot injury, turns 26 next month but believes he has a decade more of his career to come.
“I think I’ve got 10 more years,” he said.
“I went and had a spell in Finland, which was full-time and it was a great experience. I had a few full-time experiences in England, so I knew what it was like, it was just not get in the semi-professional thing.
“Unless that’s the path I wanted to take, and it wasn’t. I wanted to get back to full-time professional football and there’s nothing better for me. We get to do a great job and it’s a worldwide thing so you never know what could happen.
“Ten more years definitely I’d love to keep playing for.”
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