"There are so many - and I find it impossible to separate them," he says. He then gives you a rapid-fire synopsis, starting with the most cherished memory from his own playing career - a brilliant goal and overall performance to help England trounce the Scots 5-3 in a Wembley schoolboys international in 1960, one of David’s five caps at that level.
"I am going to have to be egotistical here - the newspapers described me as the Hammer of the Scots," he says.
Then it's on to the performances from his boyhood idol John Charles; Tottenham's 1960/61 Championship/FA Cup double winning team; and the second goal by Argentina's Diego Maradona in the 1986 World Cup clash with England.
Being such a club man, it is perhaps inevitable that he should focus on Tottenham's double triumph particularly enthusiastically, especially as he was in the crowd at Nottingham Forest - his home town club - when Spurs played their 13th league match there.
Having established a First Division record by winning their first 11 games, they were then held to a 1-1 draw by Manchester City. However, with some critics suggesting that they were likely to decline, they hammered Forest 4-0.
Pleat recalls: "If any match in England emphasised to me the way the
game should be played, it was that one.
"One reason why these sort of memories mean a lot to me is that there have been so many changes in the game since then," he adds. "Football is no longer a sport, it's a business and quite a bit of the romance has gone out of the game.
"I have always had a soft spot for Spurs but that particular team had a major influence on me. I found their approach to the game absolutely exhilarating."
By Jason Tomas, The Observer
When you get David Pleat on the subject of vivid sporting memories, it seems that our Director of Football is never going to stop.