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Gillingham’s Kent Reliance Senior Cup game at Phoenix Sports will have added significance on Tuesday night.
Their county neighbours Maidstone United await the winners in round three, hosting that tie at the Gallagher Stadium later this month.
It’s been 25 years since the two sides have met in a competitive fixture, but caretaker boss Peter Taylor won't risk his senior players for the Phoenix tie.
He said: "It won't make any difference to the team that we play on Tuesday.
"It’s nice that we could be playing Maidstone if we get a result, but we have to beat Phoenix first.
"It will be a very young team and I don’t think we will risk anyone.
"It’s good for the youngsters and I am sure all of the subs from Sunday will have a run-out, along with the likes of Ben Chapman and Aaron Simpson as well. It will be nice for them to have another game."
Gills' last meeting with the Stones was back in March 1992, in a 1-1 draw, when both teams were competing in the old Division 4.
The Stones had the upper hand in league outings, while they were briefly playing at that level, with the Gills winning just one of the six meetings between the sides.
The Gills did twice beat the Stones in the Football League Trophy, however, scoring four goals in both games.
Prior to that they met in a memorable FA Cup tie back in 1980, which Maidstone eventually won 2-0 in a second replay after two matches had failed to produce a goal.