Former Gillingham player Tim O’Shea is preparing to lead Cray Wanderers into the FA Cup first round for the first time in their 166-year history.

O’Shea played more than 100 games for the Gills between 1989 and 1992 before ending his playing career at Welling United. On Sunday, in front of the live cameras, his Isthmian Premier side host League 1 high-flyers Stockport County.

O’Shea, 59, was initially assistant boss to another former Gillingham player, Neil Smith, before taking charge in March last year. His assistant manager is former Gills boss Mark Stimson.

They’ve been on a thrilling run to get this far, including a shock win over Maidstone United in the second qualifying round.

A home victory over Chippenham Town took them to the final qualifying stage, where they needed another replay against higher-ranked opposition Bedford Town. The teams met at Cray’s Flamingo Park with the first-round draw already made and the then highest-ranked side in the competition, Stockport, awaiting the winners.

The match went the distance, finishing 2-2 and going down to penalties, where Jakob Lowe scored the crucial spot-kick.

O’Shea said: “We’ve got delivery drivers in the team, PE teachers, and they all do other bits and pieces. In the lead-up to the game we get four hours maximum with the players to prepare for Stockport, and I imagine they will have four days!

“I know the players are buzzing for it, and I am sure there will be a few haircuts and sunbeds for them and I know they will give everything.”

Cray were given a breather in the week by the league, with their match away to Dulwich Hamlet postponed.

Lowe is an injury doubt. He also scored the winning penalty during a shoot-out to decide their FA Trophy third qualifying-round game at Cheshunt, but picked up a knock for parent club Leyton Orient in their FA Youth Cup win over Chelmsford on Friday night.

With their FA Cup and FA Trophy commitments, the Wands have played only 10 league games and sit 18th in the table - a position that could be misleading if their 4-1 weekend win at Brentwood Town is anything to go by.

O’Shea said: “It’s the old saying, isn’t it? It’s the old bread and butter and whatnot.

“We tried to keep as much focus as we could for our league game. It’s only really after then that it’s started to dawn on us what we’re up against on Sunday.

“It was good to go over there and put in a good performance. We’ve got an honest group here. I was still worried [if] they would want to be going into tackles but, fair play, there were some cuts and bruises afterwards.

“Jakob Lowe’s injury was the only one really, and that wasn’t even in our game. He’s going to have a scan and if we can get him out there, there’s a place for him.”

Stockport are 113 places higher in the football pyramid and will be massive favourites, with the game live on TNT Sports and BBC2, with a 2.15pm kick-off. If you haven’t got a ticket, it’s the only place to watch as the tie was sold out within 10 minutes.

O’Shea said: “I’m pleased for [chairman] Gary Hillman and [vice-chairman] Michael Paye that they will be able to showcase the ground and if there is anybody out there local who hasn’t been down to Flamingo Park they can see it in all of its glory and with that we might get a few more along to our league games.

“There have been changes to the ground and both guys are really sensible with their money. They’re going about it in the right way. It’s going to be nice. I just hope the weather is kind to us and stays dry. It will be something else when that ground is full.”

O’Shea knows all about the FA Cup’s capacity for giantkilling, having been on the wrong end of one during his playing days at Priestfield.

He was in the Gillingham side that lost a first-round replay away to Welling United in November 1989, with the Wings then playing in the GM Vauxhall Conference League.

O’Shea did not have much luck in the FA Cup with Gillingham and also narrowly missed out on a big match in the competition during his later playing years at non-league Farnborough Town.

He was there under the management of Graham Westley, whose side had reached the fourth round and a game against Arsenal at Highbury.

O’Shea was playing and working under Westley at the time and featured in a spread in The Sun newspaper, pictured with a mop and a broom and tipped to be a key man in the game.

“They did a feature about how I was due to be playing sweeper and all that malarkey,” O’Shea recalled.

“As it turned out, I wasn’t even in the squad! I was going out on loan as my playing days were coming to an end.”

Sadly for him, his move to Welling was in the process of being finalised and he was not included in the matchday squad against the Gunners, who won 5-1 with Dennis Bergkamp among the goalscorers.

Football is littered with “what if” moments, but whatever the outcome this Sunday, nobody can take O’Shea’s achievements away from him as the first man to lead 166-year-old Cray Wanderers to an FA Cup first-round tie.

They do, though, face a daunting task. Stockport have won five of their last seven in League 1 and sit two points off the top. Keeping the Gillingham links going, they have a striker in Mikael Mandron who had two spells at Priestfield.

It’s a team littered with seasoned Football League talent but whatever the result this weekend, it will be a historic day for the club.

O’Shea said: “It will be a great occasion for us, for the club and everybody involved. The history-making side of it. The club’s older than the FA Cup!

“It’s a proud moment for everybody involved. To actually be a part of that, no one can take that away from us.”