That day finally arrived on February 7, 2004, when JD typically scored on his Spurs debut in a 4-3 win against Portsmouth. The pair played together for the rest of Ledley's career, barring Jermain's short spell at Portsmouth.
They came across each other years before that though, when they played youth football at different age groups for Senrab in East London.
From there, Ledley went to Spurs, Jermain to West Ham and after playing together for England Under-21s, they were team-mates when JD joined us in 2004.
"I always knew about this kid in Tottenham's youth team, everyone did," said Jermain.
"Before Spurs, we played together for England Under-21s and even then he was unbelievable. The game was so easy for him. I was so impressed. When I first started playing with him for the Under-21s I thought ‘wow, he’s something special’.
"When I signed, I knew Ledley from the Under-21s, he helped me settle in. I knew Anthony Gardner a little, but Ledley was the one who looked after me. It was great. That helped me when I signed for Spurs."
Much has been said about Ledley the player and the person in the build-up to his Testimonial, and one word keeps cropping up - presence.
"Ledley was calm, but when it came to matchday and he needed to say something, he would say something. And Ledley was one of those people who when he talked, people listened. He has that presence where he doesn’t need to say much anyway but when he did, everyone listened.
"That presence is something special. I remember talking to Adebayor and he said Zidane is really quiet, doesn’t say much, but when he talks people listen. Ledley’s the same."
Jermain went on to play 363 times for us before departing for Toronto in January, scoring 143 goals - placing him fifth in our all-time goalscoring list.
Ledley, of course, was a one-club man with 323 appearances between his debut in 1999 and retiring in 2012.
How many players do you get that will stay at a club for years and years, perhaps their whole career?" added Jermain.
"You don’t see that now. Players move on. He loves the club. I’m sure there were opportunities where he could have moved but he didn’t want to, because he loves the club. He loves the fans, they love him. That’s why he’s still involved, he’s Spurs through and through. You don’t get that very often these days.
"It will be a special night for him. Everyone loves Ledley."