It must be taken into account, however, that the Stones, re-formed in 1995, have only actually been back in the competition since 2002.
Jay Saunders` side made it into the hat for the First Round after a replay win against Bostik League Premier side Enfield Town.
It was a tale of three penalties and two stoppage time goals at the end of each half at the Gallagher Stadium as Enfield came within seconds of causing one of the shocks of the round in the original tie before losing the replay after extra-time at the Queen Elizabeth II Stadium 3-1, thanks to goals from Zavon Hines, Alex Finney and Jai Reason.
Maidstone`s players will be no strangers to Cheltenham`s experienced manager Gary Johnson.
He has vast knowledge of the non-League game after spells in charge of the likes of Kettering Town, Yeovil Town and Cheltenham, who he guided straight back into the Football League at the first attempt two seasons ago.
Johnson knows his players will have to keep close tabs on joint-top scorers Joe Pigott and Zavon Hines.
Pigott, originally with Charlton Athletic, Southend United and Luton, has been a great success with Maidstone before turning a loan move from one of Johnson`s former clubs, Cambridge United, into a permanent one last January.
Former Norwich and Coventry striker Hines joined the Stones in the summer and as someone who has appeared in the Premier League as recently as 2014, his signing was seen as something of a coup for Saunders.
It will be a special day too for Stones` ex-England under-20 international defender Seth Twumasi.
The 27-year-old, who started out at Chelsea, played under Gary Johnson at Peterborough, Northampton and at Yeovil and came extremely close to making it a fourth reunion.
However, after making what was supposed to be a one-off appearance for Maidstone in a Kent Senior Cup tie against Bromley in September 2016, a recent rule change meant the Robins could no longer sign him outside the January transfer window.
But when the chance came again in January 2017, Twumasi chose to remain with Maidstone.
As for players in the Cheltenham ranks, midfielder Harry Pell knows all about Maidstone from his time with Eastleigh, as does experienced goalkeeper Scott Flinders, who only joined the Robins in August from the Stones` league rivals Macclesfied Town.
But there`s one player in particular that Jay Saunders` side will be very keen to keep quiet, and that`s Mohamed Eisa, who has been a revelation since moving to Gloucestershire from under the Stones noses at Bostik South side Greenwich Borough.