Our former midfielder took on the under-17s at the beginning of the 2000-01 season following the departure of Ricky Hill to manage Luton.
The first group he coached formed the under-19 side that is now set to comprise Colin Calderwood's reserve side next season, they won their section of the Academy League - a feat repeated by his second under-17 group last season.
It is not surprising that he finds it difficult to separate the groups in terms of ability - they both compare very favourably.
"I've only done it two years and we had a good season last year with this year's under-19s - we won our section and got through to the quarter-finals last season. We've done exactly the same this year.
"The two groups are very, very even in talent. Perhaps the under-17 group has got a little bit more technique and the older group is physically stronger. So they've both got their plusses and are two half-decent groups."
Jimmy is always very quick to point out that the main priority for the Academy is not producing great teams, but putting players on the right track to first team football.
"The important thing is that we get players out of this and now it's up to these players to go on and prove they are good enough to play for Tottenham Hotspur Football Club.
"We can help them, we'll help them all we can. But it's up to them to go out and do it."
If needs be though, Jimmy will bark at his youngsters if he feels they are veering away from the main objective and not making the most of the opportunity.
"I think you're always looking at it," he admits. "I have a little moan at the kids, a little grumble, but that's part and parcel of being a footballer as well. They've taken it on the chin and laughed about it later as well.
"I don't think I'm a taskmaster. I like them to do well and if I moan at them I'm doing it for one reason - because I care. I care about them and want them to do well for themselves and Tottenham. That's what it's all about and why sometimes you have to moan and groan at them.
"I'm not nasty. If I feel something needs to be said I'll say it to them, to let them know what their weaknesses are and what they've got to work at. If I didn't do that I'd be failing them as well.
"They know me and I think we get on okay. I'm sure they've enjoyed this season with me as well."
Jimmy Neighbour finds it very difficult to seperate the two teams he has coached since returning to Spurs on a full-time basis.