Now one of the superstars of the MLS, 'Keano' is 10th in our list of all-time goalscorers with 122 goals in 306 appearances in all competitions between 2002-2011. He is one of only 16 players in our 133-year history to hit a century of goals for the club.
Harry is up to 36 goals for us after an incredible 2014-15 campaign where he scored 31 goals in all competitions, the first Spur to do since Gary Lineker in 1991-92. He twice won the Premier League's Player of the Month, was named PFA Young Player of the Year and capped it all with a goal just 77 seconds into his senior England debut in March.
He looked sharp on his return to pre-season action as well, crashing home from 25 yards against the MLS All-Stars in the early hours of Thursday morning.
Already a three-time MLS champion, Robbie remembers Harry as a youngster coming throug the Academy ranks at Spurs and has watched his progress carefully from across the pond.
"He's been brilliant and I'm delighted for him," said Robbie. "I really hope he does well. He had an amazing season and he’s a good lad as well, I like him a lot.
"He has a good head on his shoulders and it’s just the start as well. It’s up to him now."
Robbie felt Harry's spells on loan, gaining experience at Leyton Orient, Millwall, Norwich and Leiceser before breaking through at Spurs were key to his progress.
"It just goes to show it doesn’t matter where you go on loan, it’s all experience, you get minutes, you play first team football. He got his chance and bang, he scored all those goals."