The Owls were dumped out of the competition, losing 2-1 to League Two Oldham Athletic after extra time at Boundary Park.
It was a disappointing way for Challinor to start his Wednesday reign. Challinor, who made four changes to his starting line-up, was unhappy with their first half performance.
He told the media, "I'm really frustrated and disappointed not to have won. The first half was like a testimonial. It was miles too slow and it was nothing like the team I want it to look like, which I can maybe sort of accept a little bit.
"Second half was much better. We probably had our best spell when we conceded. The subs came on and changed the dynamic of the game. It would have been great to be able to start in that manner or with that personnel, but we were unable to do so.
"And then I suppose there's always been a problem in terms of conceding goals. We've conceded two really soft goals, and that has to stop. I think as the game went into extra time, it became more of a tendency to not be as aggressive in terms of moving the ball or putting the ball in areas. Maybe because of the physical part of what that looks like, and that needs to get a whole lot better."
Calum Kavanagh fired the Latics into a 66th-minute lead only for Davis Keillor-Dunn to level the match and send the tie into extra time… But Will Sutton's 109th minute header proved decisive and stretched the Owls' winless run to five matches.
"You can't get away from the two goals we have conceded; they are really bad goals," admitted Challinor. "Regardless of what league you play in, who you play against, you have to compete. The behaviours that the players spoke about before I was even in the building are out compete, outrun, and outplay, and outfought.
"You have to do that as a minimum. We'll have to do that against Plymouth on Saturday, and without being disrespectful, Plymouth are a better team than Oldham are. The league status says that's that's the case so you have to do that as a bare minimum. We have got to get miles better at doing that otherwise, the stuff you do on the ball will count for nothing."
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I know it’s classic but we have got to concentrate on the league, yes it’s disappointing but we need players back and some practice time. This game and Jersey Mikes means nothing to me in these circumstances. 🦉🦉🦉