Chesterfield started their pre-season friendly campaign with a 3-4 loss to Cypriot side Apollon Limassol in Hungary, but with plenty of positives to take from the game.The Cypriots made an ideal start to the match as after Sam Hird half-cleared a header, Ioannis Pittas was able to lay back to Anton Maglica who blasted home a well-hit half volley from the edge of the box.
The lead didn't last long, however. A Gboly Ariybi cross from the right was heading towards Ebanks-Blake but was needlessly handled by an Apollon defender, a penalty awarded as a result. O'Shea stepped up from 12 yards and struck low and sweetly to level the contest.
Three minutes later and a similar pattern gave the Spireites the lead. Ariyibi exchanged passes with O'Shea and the winger delivered a pinpoint cross that Ebanks-Blake smothered home from six yards.
After Joao Pedro Guerra Cunha and O'Shea had seen efforts saved, Apollon were level again. Maglica again did the damage as he was allowed too much room in the Spireites' area and was able to swerve a neat shot home from 16 yards.
The Cypriot side's front two were constant aggressors and Pittas played a major role as Apollon once more took the lead, still with under 30 minutes on the clock. Getting to the byline he was able to drill across goal which the stretching Hird was only able to put past his own goalkeeper.
Chesterfield were looking comfortable in possession, but less so when the Cypriots pushed forwards at pace, Arkadiusz Piech forced a good save while Pittas saw a venomous volley blocked by Dion Donohue, playing at left-back, before the interval.
Nine changes at the break saw only Liddle and Ariyibi remain in the side from the first half, and Humphreys, playing at right-back, came close to an acrobatic equaliser within minutes of the restart when a Reece Mitchell cross found him at the back post, but the veteran fired over.
Rai Simons was next to go close, backheeling impishly but seeing his effort saved down low, with Ryan Fulton saving solidly at close range from Psycas Petros at the other end.
While it was the Spireites in the ascendancy midway through the half, the next goal came the Cypriot side's way, when Luka Stojanovic finished with power in the area to give Apollon a two-goal lead.
With the Spireites' defensive trialist leaving the field with a knock Chesterfield were forced to play 25 minutes with ten men, defending well against an Apollon side smelling blood.
Despite their numerical disadvantage, a Simons charge with five minutes left brought the Spireites back to within a goal of the Cypriots. His run from deep in his own half opened the defence and his deft slide rule pass through was perfect for
Kristian Dennis to roll past the advancing 'keeper.
Chances of an unlikely late Chesterfield equaliser were undone by the referee's final whistle, with a narrow defeat by the odd goal in seven to start pre-season for the Spireites.
Chesterfield: Triallist (gk) (Fulton 46') - Donohue (Jones 46'), Hird (Raglan 46'), Evatt (trialist 46'), McGinn (Humphreys 46') - Ariyibi, Banks (Dimaio 46'), Liddle (c), Gardner (Mitchell 46') - O'Shea (Simons 46'), Ebanks-Blake (Dennis 46')
Chesterfield: O'Shea 10' (pen), Ebanks-Blake 13', Dennis 84'
Apollon Limassol: Maglica 4' 24', Hird 27' (og), Stojanovic 68'