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Gillingham were beaten by non-league Woking in their last major pre-season test on Saturday.
Gavin McCallum put Woking ahead in the first half and Gavin Williams added a second from the penalty spot.
The Gills’ afternoon was made even worse when Anthony McNamee hit a third in stoppage time.
Martin Allen named a strong side for the visit to Conference side Woking, with Cody McDonald starting up front with Antonio German.
Stephen Gregory returned to the defensive midfield role, while Amine Linganzi pushed further forward.
With a week to go until the start of the Football League season begins, the Gills were looking for a morale-boosting performance.
Their last three pre-season outings had ended in defeat, against higher-league opposition, in Ipswich, Millwall and Crystal Palace.
Striker McDonald was involved in Gillingham’s best moments of the first half but Allen’s men went into the break a goal down.
German and Linganzi fired early chances wide and McDonald was unable to head Matt Fish’s cross on target.
Woking defender Jack Parkinson was lucky it was a friendly match, as he got away with just a warning, after pulling McDonald down. The Gills man had broken free with no other markers close but from the resulting free-kick, Chris Whelpdale fired into the wall.
With half an hour gone, home trialist John Akinde headed a good chance straight at Gills keeper Stuart Nelson but moments later they went ahead.
McCallum chased a ball over the top, shrugged off the attention of Gills defender Joe Martin and then lobbed the ball over Nelson and into the net. Woking held onto their lead for the final 10 minutes of the half.
The Gills started the second half well, with Gregory firing a couple of shots wide, while Whelpdale stung the keeper’s hands from distance.
But within six minutes of the restart, Woking scored a second. Leon Legge was harshly adjudged to have tripped Akinde and from the resulting spot-kick Williams fired into the roof of the net.
McDonald came close to halving the deficit, with a powerful shot towards the top corner, having left defender Adam Newton on his back but keeper Arran Howe parried it away.
Allen introduced a third striker with 20 minutes left, as Kedwell came on to add more options upfront for the League 1 side.
But it was midfielder Charlie Allen who had a couple of chances for the visitors. A good chance was lifted over the bar and with seven minutes left he had sight of goal again, latching onto Akinfenwa’s lay-off and shooting at the keeper.
Kedwell’s appeal for a penalty in the latter stages fell on deaf ears, following a shove from Woking’s George Frith.
Woking hit a third in the third minute of injury time as McNamee lashed in a shot from the edge of the box.
Gillingham: Nelson, Fish (Butcher 66mins), Martin, Barrett, Legge, Gregory (Kedwell 72mins), Linganzi, Dack (Allen 56mins), Whelpdale (Miller 81mins), McDonald, German (Akinfenwa 56mins). Subs: Davies, Grant, Parter, Howard.
Woking: Howe, Newton (Steer 75mins), Nutter (Wright 75mins), Ricketts (Frith 46mins), Parkinson (McNerney 56mins), Johnson (Cestor 56mins), Sawyer (McNamee 66mins), Payne, Akinde (Taylor 66mins), Williams, McCallum (Sole 66mins). Subs: Beasant, Thompson.
Attendance: 654