The two sides could not be separated when they locked horns at the home of Chester earlier this month, so another game is required to determine which team will advance to the second round of the tournament.
Match preview
York play a division higher than their opponents on Tuesday, with Neal Ardley's side members of the National League, while Chester currently operate in the National League North.
The home side have found it difficult to show consistency in the league this season, though, with a total of 19 points from 19 matches leaving them down in 19th position in the table.
The Minstermen will enter this match off the back of a win, though, having scored two unanswered goals away to Fylde in the National League on Saturday afternoon.
York are unbeaten in their last three games, including the goalless draw with Chester on November 4, with their last loss proving to be the 4-0 reverse at Chesterfield on October 24.
Boasting home advantage and operating at a higher level, the hosts will be the favourites on Tuesday, and they have only been beaten in one of their last five fixtures in the FA Cup.
Chester, as mentioned, currently play in the National League North, with a total of 23 points from 15 matches this season leaving them down in 14th position in the table.
The Seals finished third in the National League North last season, which saw them secure a spot in the playoffs, but they were beaten by Brackley Town in the semi-finals.
Calum McIntyre's side had actually been on a six-game winning run in all competitions ahead of their clash with York in the first round of the FA Cup, but the two sides could not be separated.
Chester were then beaten on Saturday afternoon, going down 3-2 at Darlington, with the loss proving to be their first since September 23 against Boston United.
The Seals are unbeaten in their last four games in the FA Cup and have already overcome Tadcaster Albion, Nantwich Town and Hartlepool United to advance to the first round of the competition.
York City FA Cup form:
York City form (all competitions):
D
L
L
D
D
W
Chester FC FA Cup form:
Chester FC form (all competitions):
W
W
W
W
D
L
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Team News
York head coach Ardley will need to assess the fitness of his players following the two-goal success over Fylde in the National League on Saturday afternoon.
Lenell John-Lewis was only a late substitute in the league last time out, but the 34-year-old is expected to lead the line on Tuesday night.
Quevin Castro and David Stockdale should also come back in, but the likes of Alexander Woodyard and Oliver Green will keep their spots in the XI.
As for Chester, there will be changes to the side that took to the field for the first whistle against Darlington, with McIntyre potentially naming the same XI that started the clash with York last time out.
Adam Thomas and Reece Daly are both expected to be in the side, while George Glendon and Elliott Whitehouse, who have been in strong scoring form from midfield this term, should also start.
Declan Weeks, meanwhile, is also expected to be given the nod to feature from the first whistle.
York City possible starting lineup:
Stockdale; Fallowfield, Cordner, Howe, Smith, McLaughlin; Castro, Woodyard, Green, Kennedy; John-Lewis
Chester FC possible starting lineup:
Stanway; Sparrow, Edwards, Williams, Taylor; Weeks, Roberts, Whitehouse; Glendon; Thomas, Daly
We say: York City 2-1 Chester FC
This is a really difficult match to call, as Chester demonstrated in their clash earlier this month that they can compete with York. The home side can call upon the greater quality, though, and we are expecting the National League side to shade a close match on Tuesday night.