However, their six-year reign as a League Two outfit is now nearing an end in the town of Annan tonight.
The Citizens are just 90 minutes from securing promotion to Scottish football's third tier with goals from Innes Murray and Ryan Shanley handing the Capital outfit a deserved first-leg advantage.
Watching on at Ainslie Park earlier this week was the man at the helm when City upset the apple cart to bring East Stirlingshire's 61-year association with the Scottish senior leagues to a halt.
And now Gary Jardine, who left the club in 2017 and is the current manager of Lowland League outfit Civil Service Strollers, is urging his former side to make history in the Dumfriesshire this evening.
"Getting promoted to League Two was a very proud moment, not just as manager but I was there for 16 years having played too so you love the club," Jardine told the Evening News. "For all the hard work that goes on and off the park, I'll be as happy as anyone if they manage to do it tonight.
"I honestly believe Covid has maybe got in the way a wee bit or they might have managed it even earlier. Obviously, there are other circumstances with the likes of Kelty coming into the SPFL with their spending power, but it was always the goal of myself and the chairman (Jim Brown). He's very driven and Edinburgh City through and through and we had hoped over the course of five years the club would be knocking on the door of League One.
"Hopefully now is the time they do go up. If you look back at the club over the past ten or 15 years, it's been continuous improvement. Momentum plays a huge part in football and I think they've had a lift just at the right time."
Jardine believes interim boss Alan Maybury has brought a much better balance to the side since replacing Gary Naysmith in March.
"They've got a real good chance now," he said. "Annan are chasing the tie so City will have no fear. Everything is pointing in the right direction so fingers crossed they can do it. Annan have had a fantastic season themselves and have produced results when it's least expected, so it's not a given by any means.
"But having the firepower that City have with Shanley, (John) Robertson and Ouzy (See), it's difficult to see them not scoring down there. If Annan go gung-ho then those three will have more than enough chances. Alan's side are now carrying a far greater threat up top.
"The recruitment in January was another big factor and they've managed to get key players back from injury. Shanley has been a big player and he's still got a bit to find, but I believe he is a top-flight player. I had him for a period at Strollers and he's a huge talent. Their captain Robbie McIntyre is also back so that has been a boost too.
"League One is as tough as any league in Scotland. If they can have the likes of Falkirk and Dunfermline coming to Meadowbank next season, clubs when I was growing up that were Premier League sides, it would give the place a huge buzz."