Sheffield United manager Chris Wilder has described the club’s upcoming FA Cup fixture against Fleetwood Town as a challenging and uncomfortable assignment. The match is scheduled to kick off at 7:45 p.m. and will be broadcast live on Sky Sports.

Fleetwood, currently competing unbeaten in League Two, feature several former Sheffield United players, adding a familiar yet difficult element to the encounter. Wilder expressed that preparing for the fixture presents unique difficulties compared to facing higher-tier opponents.

“This is an awkward and uncomfortable tie for us,” Wilder said, referencing a previous experience in the FA Cup when Sheffield United faced Millwall away six years ago. After that match, Wilder spoke with Gary Rowett, then Millwall’s manager, who remarked that clubs often prefer matches against Premier League opponents who might not field their strongest teams. “That isn’t the tie we really wanted,” Rowett noted, according to Wilder.

Wilder explained that matches against Premier League clubs can sometimes be more straightforward because lower-ranked sides can approach the game without pressure, seeing themselves as underdogs with little to lose. In contrast, he said, Sheffield United enter the fixture with “everything to lose,” increasing the stakes and making preparation more complex.

The manager’s comments underscore the unpredictable nature of cup competitions, especially when higher-ranked teams play lower-division sides, and highlight the mental and tactical challenges Sheffield United face on what Wilder terms an “awkward” trip to Fleetwood.