That year, the Hammers beat Coventry City 9-1 in the final over two legs - and Chris Kirkland was in goal for the Sky Blues.
"It was a great night, still vivid in the memory, and it was a great year with some great players and great victories," remembers Tony.
"I just hope this team can go some way to copy the side of '99. We are in the last 16 and hopefully we can get in the last eight, but it will be a tough game tonight against a well organised side.
"I can't see many goals - famous last words - and it wouldn't surprise me if it went all the way to extra time and penalties.
"That is how tight I think the game is going to be - but someone has to unlock the door and let us hope it is us.
"I think the team of four years ago had a lot more flair with the Carricks, the Coles, and the Garcias, a looser system in terms of giving them more freedom.
"We played a 3-5-2 or sometimes a 5-3-2 depending on the situation, so we had lots of interchange and creativity in the middle of the park.
"This side has, perhaps, has not got the flair but has got a bit more organisation about them. It is more functional, which is not to say we haven't got good players, but I do feel our strength is in our defenders.
"I think we have got some excellent defenders in Elliott Ward, Tommy Laws, Anton Ferdinand, young Brent Tattum at left back - a good solid defensive grouping.
"I think it will be many years before we find a team as good as the '99 one.
"I remember hearing Gordon Strachan on the radio after the Coventry game saying he has seen better players individually but he has never seen a better team at youth level in his whole youth career, which was a fantastic compliment to us.
"I will go along with that - we were a very good team."
The current crop is an efficient unit, however, and Tony adds: "It is horses for courses but if you keep clean sheets you have got a chance of winning football games.
"Sometimes in youth games, unlike ones at the very top level, players' nerves come into it and a couple of mistakes can cost a game even if you played well.
"There is not the experience, say, to snap out of a poor start and it costs the game.
"We have done a lot of preparation, a lot of team work, got our pattern of play, and watched videos of the opposition.
"So let's hope it is all right on the night.
"It's funny because a few years ago we were always producing quality midfielders and forwards and I remember saying to Jimmy Hampson, our head of recruitment, 'Jim, when are you going to find me a big, ugly centre half?'
"He said they were doing their best and three or four years down the line there is a real influx of good defenders with Glen Johnson, who has just broken through into the first team, being one of them.
"Not that he's ugly, though!"
*Come and support the kids in their FA Youth Cup clash against Norwich City at Upton Park tonight. Kick-off is at 7pm and entrance is via the Dr Martens Stand lower tier only. Prices are £3 for adults and £1 for under-16s and OAPs.