Hosting Northampton Town at the LNER Community Stadium this Saturday, York enter the FA Cup at the first round looking to progress past their fellow League Two side.
It's a competition which City haven't seen much success in in recent years - with a second round tie against Wigan Athletic being the furthest they have reached in the last 16 years.
But the Minstermen have plenty of good times to look back upon.
Here's our pick - and videos - of some of York's greatest home ties in the FA Cup.
York City 3-1 Tottenham Hotspur - 1955
Those who can remember this incredible Bootham Crescent meeting will look back upon it with great fondness.
A crowd of 21,000 people packed into the ground to watch York topple First Division Spurs, in an FA Cup run that saw City go all the way to the semi-finals.
They had trailed to Tottenham, with George Robb putting the visitors ahead.
But a magnificent effort from the Minstermen saw them turn the tie on its head - with goals from Norman Wilkinson and Billy Fenton putting York in front, before Wilkinson steered in Fenton's cross for the third.
After the game, Spurs' Danny Blanchflower said: "York's standard of play left us speechless."
York City 0-0 Huddersfield Town - March 1938
A goalless draw might be looked upon with disappointment, but this was a record-breaking afternoon for City.
Hosting another Yorkshire side in Huddersfield, the Minstermen marked their record attendance at Bootham Crescent, with an incredible 28, 123 supporters through the turnstiles.
York did come close to a winner as Peter Spooner had a late header cleared off of the line, but instead settled for a replay, where they lost 2-1 in West Yorkshire.
York City 1-0 Arsenal - January 1985
Up there with one of City's greatest-ever giant-killings was when the Minstermen stunned the footballing world to beat Arsenal at Bootham Crescent.
Hosting top flight Arsenal, Keith Houchen's penalty was enough to fire York into the fifth round of the FA Cup - earning a tie with another giant in Liverpool.
The Arsenal team consisted of eight internationals and had cost more than £4.5 million to assemble - a huge fee back then - but they couldn't break down City's squad at a snowy Bootham Crescent.
York City 1-1 Liverpool - February 1985
One month on from their Arsenal heroics, York came so, so close to taking the scalp of another footballing giant.
They would go on to lose a replay to Liverpool 7-0, but City succeeded at Bootham Crescent in holding their star-studded visitors to a draw.
With players like Ian Rush and Kenny Dalglish arriving to North Yorkshire, it was the heart of York that managed to earn the replay.
Ricky Sbragia levelled the scores after Rush's opener in another fantastic FA Cup clash.
York City 3-3 Southampton - January 1971
In 1971, this was a huge David vs Goliah meeting as Division Four York welcomed First Division Southampton to Bootham Crescent.
A goalless opening 45 exploded into life in the second-half, as the Saints broke the deadlock with Jimmy Gabriel heading past City goalkeeper Ron Hillyard.
Mick Channon, an England international, then doubled Southampton's advantage with 12 to go and it looked to be over for York.
They showed fight as Kevin McMahon halved the deficit just two minutes later, but a quick response from Southampton saw their two goal lead restored as Ron Davies bagged a third.
City weren't done though - Dick Hewitt first fired home to make it 3-2 with three minutes to left, and with a minute to go, Paul Aimson found the inside of the post to earn a dramatic replay.