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Gillingham were beaten by a relegation-threatened side for the second match running on Saturday.
The Gills found themselves two goals down before the break.
Sylvan Ebanks-Blake bundled in the opener before Lee Novak smashed home a stoppage-time stunner.
Emmanuel Osadebe halved the deficit late on, but Gills couldn’t find a way to level the game.
It was the first time since September that the Gills have lost back-to-back league matches.
More worrying for the Gills will have been the sight of star player Bradley Dack limping away injured during the first half.
Central defender Adam El-Abd made his debut for the Gills, coming into a defence that included returning Ryan Jackson - back in the side having recovered from injury.
However Jackson ended the game in discomfort, pulling up after shooting over late-on.
Gillingham had hopes to get back to winning ways on a home ground which had served them well this season. Josh Wright captained the side in the absence of John Egan and Doug Loft.
They started the match positively enough, with Dominic Samuel putting a good chance over in the opening minute. Rory Donnelly also came close, but Tommy Lee saved.
Max Ehmer came close with a shot that was turned onto the upright before Chesterfield’s American winger Gboly Ariyibi started to pose problems, drawing fouls from Ehmer and Jackson, both which earned the Gillingham players bookings.
The Gills lost their leading scorer Dack to injury midway through the half. He went down in a heap with nobody around him and limped off towards the changing rooms, replaced by George Williams.
If that wasn’t bad enough, Chesterfield took the lead just three minutes later.
It was from an Ariyibi cross that Chesterfield got the advantage. He whipped the ball in for Ebanks-Blake and the forward did just enough to force it over the line.
Wright fired wide from distance for the Gills but chances were wasted from the hosts, failing to make a anything from a couple of corners.
And in the third minute of first-half stoppage time Chesterfield doubled their lead. Novak got onto the ball from 25 yards out, picked his spot and made it 2-0.
Bradley Garmston came on for the second half as the Gills changed their shape. Aaron Morris dropped into a back-three for Gillingham, leaving Garmston and Jackson to attack more.
The two wide players were instantly involved as Garmston’s cross was headed down by Jackson, but keeper Lee saved. He was also there to deny Samuel as he headed at goal.
Substitute Luke Norris tested Lee from distance as the Gills enjoyed most of the possession in the second half. Turning that into a goal wasn’t proving easy, however.
With 10 minutes left the Gills finally got on the scoresheet as Osadebe headed in a left-side cross from close range, scoring only his second goal for the club.
Donnelly headed over a great chance with the goal at his mercy from Jackson’s cross as the Gills surged forward in the latter stages. It was the closest they got.
Gillingham: Nelson, Jackson, Chicksen (Garmston 46mins), Ehmer, El-Abd, Wright, A Morris, Osadebe, Dack (Williams 33mins), Donnelly, Samuel (Norris 63mins). Subs not used: G Morris, Hessenthaler, Oldaker, List.
Chesterfield: Lee, Hird, Ebanks-Blake (Donohue 67mins), Novak, O’Neil, Dimaio, Anderson, Banks (O’Shea 84mins), Talbot, Ariyibi, John. Subs not used: Chapman, Gardner, Humphreys, Simons, Slew.
Attendance: 6,012 (199 away)