The defeat against Woking leaves them 23rd in the National League.
Chesterfield remain without a win this season in the National League after losing 2-1 at home to Woking last night.
The result prompted John Sheridan to apologise to the club's fans after the game, as he admitted his side weren't good enough to secure their first victory of the 2019/20 campaign.
Sheridan made one change from the Spireites 2-2 draw at Boreham Wood, with Robbie Weir replacing the suspended Laurence Maguire in the middle of the park.
After an uneventful first half, the visitors struck first when Ibrahim Meite bundled home a Tyreke Johnson cross on fifty-two minutes.
Then on sixty-one minutes, Woking doubled their lead through a Dave Tarpey free-kick, which he struck well from twenty-five yards out.
The Spireites scored a late consolation through Scott Boden, as he nodded in with three minutes remaining to get his third goal of the season.
However, it wasn't enough for Chesterfield, who've now secured just two points from a possible twelve in English football's fifth tier.
Speaking afterwards, Sheridan admitted there's plenty to work on;
"The performance wasn't good enough to win the game.
"We passed it okay at times, I think the only time we played with any endeavour and pace was in the last twenty minutes when we were 2-0 down, which should never be the case.
"I've got to look at who I'm going to play from now on, I need to try and get one or two players in if I can.
"I need to have a word with the Chairman and the people upstairs, because I feel we need a bit of freshness in the squad.
"I'm giving people opportunities and we're getting the same results, our game is too slow right now."
Chesterfield return to action on Saturday away at Barnet.