It was the 2009-10 season, Jermain's best in a Spurs shirt, a campaign that would include his five goals against Wigan, three hat-tricks and end with 24 goals as we qualified for the Champions League.
At the same time, a raw 16-year-old was banging in the goals for our Under-18s. In his first season in the Academy, Harry racked up 18 goals in 22 matches.
Jermain eventually left for the MLS and Toronto in January, 2014 having climbed into the top five of our all-time goalscorers with 143. A few months later, April 2014, Harry scored his first goals for us in the Premier League.
Three full seasons later, and Harry is ripping up the record books as he goes along. He's hit 20, 25 and 29 goals in the Premier League alone, winning back-to-back Golden Boots. He scored 35 in all competitions last season, the best total since Clive Allen's record 49 in 1986-87. He scored five hat-tricks and he's up to 99 goals for the Club.
Below: Jermain with the matchball after his five-goal haul against Wigan - November, 2009
He's 'one of our own' and Jermain, 34, who scored another 17 goals despite Sunderland's relegation last season, is relishing watching 'H' deliver. Seven years after that 2009-10 season, the pair are together in England's squad to face Scotland (Saturday) and France (June 12).
"It’s not easy to score goals in the Premier League," said Jermain, speaking to us after the Lane's Finale. "The league is so strong, home and away, so to score three 20s on the trot...I just think he’s in the perfect team, no team is going to create more chances and dominate games like Spurs.
"If there is one team to be at right now, it’s Spurs and with ‘H’, I said ages ago he was a finisher.
"I said to the guys how good he was and if he got the chance, he would score goals. I’m not surprised with how well he’s done. That team creates chances and give him a chance and he’ll score."
Harry is right out of the Defoe school of strikers with an almost insatiable appetite for goals. Like Jermain, Harry is always working on his finishing after training. He relishes every goal scored in training or on the main stage. You can't imagine Jermain walking past an empty can without hitting it into an imaginary goal - Harry is the same.
"That hard work has got him to where’s got so far, sheer hard work, just wanting to score goals, that’s someone who just loves to score goals," added Jermain.
"That’s just in you, and you keep practising and then in a game, it comes naturally and that’s why he scores so many goals.
"He’s strong, he’s big, H. He’s grown a lot! I never had that height! For someone that size, his balance...a lot of the time you see him and he’s got the ball, holding defenders off and he looks off balance but they still can’t get the ball off him because he’s so strong.
"After all that, he always gets his shots off, all dfferent angles and always hits the target. That’s what they say about him, he always hits the target, both feet as well.
"He's so young as well! I can't see anything else but him just continuing to score goals for Spurs."