There he is, on his 37th birthday, putting "Darlo" ahead in the first match - still the only occasion on which they have featured live on television - and against his first club as well. Spool back and here's a younger looking Gary walking out at Wembley in Sunderland colours for the 1992 final against Liverpool, emulating his brother Dave's (more successful) appearance for Coventry against Tottenham five years earlier.
The family video will need to be set again for Match of the Day on Saturday night, even if this time the Bennett contribution to an historic occasion is confined to touchline shots. Gary, 38 yesterday, has appeared in the back-four once or twice this season, but reluctantly accepts that only a flu epidemic or injury crisis will get him into the side for the tie at Aston Villa - after all, why change a lucky losing team? "It's time for our younger players to sample the special magic of the Cup," he said, after Tottenham's secretary and FA Cup committee member Peter Barnes had put in his thumb and pulled out a plum worth some pounds 200,000 to the Quakers.
Youngsters and old sweats alike will love it all if their reaction to the news last Wednesday was anything to go by. A serious training session collapsed into chaos after the club physio raced on to the pitch bellowing: "We've got the wild card." A car driven by the defender Adam Reed was then stopped by police because his team-mates in the back were celebrating so enthusiastically.
The manager David Hodgson, having set his heart on promotion from the Third Division after finishing 11th last season, has distinctly mixed feelings, but Bennett is clearly in love with that old Cup magic. "It really drove it home to me playing in the 1992 final how big the competition is," he said. "You couldn't help but be aware it was being shown all over the world. Ask any youngster kicking a ball about what they'd love to achieve and they'd say 'playing in the FA Cup final'. I've got a losers' medal, but nobody can take away the fact that I played in the final. In the same way, our young lads can now collect some memories of playing at Villa Park, a ground that hosts the semi-finals."
There is no hint of embarrassment, either, at making this peculiar little piece of Cup history after being so well beaten in the previous round by Gillingham, who now have a much less glamorous tie at Walsall. Bennett insists: "The FA Cup has always been about the luck of the draw, if not quite in this way. Some teams are lucky to get through, others are unlucky to go out. Darlington have never had much luck down the years, so we'll gladly take this."
Indeed, having played for only two of their 116 years outside the lower divisions and been relegated to the Conference for one season a decade ago, the club went into 1999 convinced that they were due a better hand. It was finally dealt last May, when George Reynolds, Sunderland supporter, former felon (four years for safe-breaking) and now one of the country's wealthiest men, bought control. On his first day, he shooed away the bailiffs and paid off pounds 5m worth of debts. For once the Feethams loyalists had got a lucky break.
But as Gary Bennett says: "Football's not always about what you deserve. It's grabbing the opportunities that arise." Having already defied odds of 20-1 in a lucky losers' draw, Darlington will go to Villa Park determined to seize the day.