Midfielder Scott Kerr could return to York's starting line-up for the first time in seven months in the Johnstone's Paint Trophy clash with Coventry.
Kerr, sidelined since damaging his cruciate knee ligament in March, returned to the squad for the goalless home draw with Rotherham at the weekend and duly stepped off the bench midway through the second half.
Manager Gary Mills has hinted Kerr is ready for a longer run-out as he looks to build up his match fitness.
New loan signing Danny Kearns, joined from Peterborough last week, also appeared as a second-half substitute against Rotherham and could make his first start for the club against Coventry.
Summer signing Oli Johnson could be handed his full debut if Mills opts to rest some of his regular starters, with midfielder Jonathan Smith and defender Clarke Carlisle also hoping for recalls as York chase only their second win in eight matches.
Callum Ball's second-half cameo at the weekend is likely to earn him a spot in Coventry's starting XI.
The on-loan Derby striker, who celebrates his 20th birthday on Monday, stepped off the bench at half-time against Bournemouth to change the complexion of the game in City's favour, helping secure a 1-0 win - the club's first at home in the league this term.
Ball's effective performance is set to see him promoted to manager Mark Robins' starting XI at Bootham Crescent as the two sides meet for the first time in 52 years for a place in the northern section quarter-finals.
Midfielder Kevin Kilbane, fit again after a hamstring complaint, could also come back in along with the likes of Chris Hussey, Reece Brown, Cyrus Christie, Steven Jennings and Stephen Elliott.
However, winger Gary McSheffrey, striker Cody McDonald and centre-back William Edjenguele will each again be assessed.
Coventry triumphed 5-2 in their most recent meeting with the Minstermen in 1960. It was the last of only five encounters between the two sides down the years, with York's only win coming in an FA Cup tie way back in 1938.