Substitute Adam Smith fired Chesterfield to victory and left Yeovil still searching for their first win.
Yeovil went ahead when Luciano Alvares scored from close range but Paul Hall levelled just before half-time.
Smith put Chesterfield 2-1 up from a corner after 53 minutes and then stole round a sleepy defence for his second.
Yeovil were awarded a penalty late on when keeper Barry Roche fouled Kevin Gall but Roche redeemed himself by saving Pablo Bastianini's effort.
Yeovil: Weale, Amankwaah, Lockwood, Skiverton, Miles (Harrold 69), Lindegaard (Poole 45), Way, Johnson, Jones, Bastianini, Alvarez (Gall 69).
Subs Not Used: Terry, Collis.
Goals: Alvarez 36.
Chesterfield: Roche, Picken, Blatherwick, Hazell, Nicholson, Davies, Allott, Niven, Hall (O'Hare 76), Folan (Allison 65), Hurst (Smith 45).
Subs Not Used: Larkin, Muggleton.
Booked: Folan, Niven, Roche.Goals: Hall 44, Smith 53, 75.
Ref: P Taylor (Hertfordshire).