Graham, who arrived at White Hart Lane in October 1998 (see picture), put down “quite good but could do better” on his report card to mark the milestone.
The Scot, who won two league championships with Tottenham’s north London rivals Arsenal, talked to Sky Sports Centre in an interview screened on Sky Sports 1.
“A lot has been done but I would have liked things to have moved a bit quicker - I am a bit disappointed with that aspect,” said Graham, who won the League Cup in his first season in charge.
“We’ve done quite well but could do better. I think the playing side of the club is a lot healthier now than two years ago but we’re way, way short of a top squad to challenge Manchester United and Arsenal.
“It’s been too long since Spurs were challenging for championships. Spurs were one of the big clubs a decade ago when Terry Venables was manager. Unfortunately, things have slipped since then but we’re not the only big club looking to catch the top teams — Everton and Newcastle are in the same boat."
Graham had some encouraging words for Spurs fans about Sol Campbell and Steve Carr, two defenders he does not want to lose.
Campbell’s contract expires next summer while Carr is after a pay rise after being one of the Premiership’s most consistent full-backs over the past two years.
Graham is certain Carr will stay at White Hart Lane and thinks Campbell may surprise a few people and also pledge his career to Tottenham.
“Steven Carr is still on a long contract, he has been outstanding for us since I’ve been at the club. We are trying to improve his contract and he will be at the club, there’s no question about that,” said Graham, relaxed after a brief holiday in Dubai with his wife.
“I just don’t know what Sol’s intentions are — I just don’t know. It’s the modern way, players will see their contract and see who comes in with the best offer. But I would like to think Sol will sit down with us at the end of the season.
“Everyone is anticipating he will go but I think there is a good chance he will stay. I wouldn’t want to lose him. We need him to be a cornerstone of the season.”
Graham, who is backing his old pal Venables for the vacant England manager’s job, will have fellow Scot Gordon Strachan in the opposite dug-out at Highfield Road.
And he admits he is a fan of Strachan’s excitable touchline manner. “Gordon lives football. Like a lot of Scots, he is passionate and I think that’s nice for the game generally.”
Spurs manager George Graham celebrates his 100th match in charge of the club at Coventry on Saturday admitting: “We are way, way short of having a squad to compete with the top clubs.”