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Goalscorer Vadaine Oliver limped off injured as Gillingham crashed out of the Carabao Cup on penalties to League 1 rivals Cheltenham at Priestfield.
Oliver had put the hosts infront but just four minutes later the Robins were level. An injury to Oliver led to defender Max Ehmer playing upfront for the second half but the tie went to penalties and Cheltenham scored all five of their spot-kicks to progress.
Gills boss Steve Evans made changes from the weekend, as expected, but Covid issues kept the young stars of the previous round, Harvey Lintott and Gerald Sithole, out of the squad.
The Gills manager showed his determination to win through to round three - and a potential money-spinning tie - as he named some of his big hitters including striker Oliver, albeit the only fit out and out striker at his disposal.
It must have been his worst fear to see Oliver pick up an injury.
Among the five changes to Evans’ side was the return of David Tutonda at left-back following his suspension at the weekend, but he lasted only 35 minutes before limping off injured.
Cheltenham - the champions of League 2 last season - made seven changes. Former Chatham and Hythe striker Alfie May lined up for the visitors.
Oliver appeared to pick up an ankle injury when heading his side infront, rising highest to head home Olly Lee’s deep cross. He managed to make it to the break before being replaced.
Prior to his opener, Oliver had an earlier chance but was unable to make a decent contact as the ball fell for him after Ben Reeves had blocked a Ben Tozer clearance.
The lead that the Gills got lasted only four minutes as the defence failed to deal with a long ball forward, which was helped into the path of Kent-born May and he slotted it home.
Neither side got many more opportunities in front of goal.
Gillingham changed things for the second half with Jack Tucker replacing Oliver and centre-half Ehmer playing as a makeshift striker.
Danny Lloyd glanced a chance over for the Gills at the start of the second half and Ellis Chapman shot wide for the visitors as the game opened up after the turnaround.
Gills keeper Chapman hung onto a header from Lewis Freestone as Cheltenham looked to use set-pieces to their advantage, particularly the long throw. Bailey Akehurst did well to block a shot as the visitors broke and Robbie McKenzie also had to get in the way of an effort as the patched-up Gills found it hard going at times.
Callum Wright sliced a good chance wide for Cheltenham before Evans made his last change, putting weekend man-of-the-match Mustapha Carayol on.
Cheltenham had a few players go down in the latter stages as the clock wound down to the inevitable penalty shoot-out. With no extra-time, it was straight to penalties.
The visitors could have still won it in stoppage time, after Rhys Bennett lost possession, but George Lloyd sliced the ball wide with just the keeper to beat. Even later into time added on, the Gills felt a push on Bennett in the opposite box should have led to a penalty.
Gillingham had seen off Crawley from spot-kicks in the previous round and this one was also to be decided by the lottery of penalties.
It wasn’t to be Gills’ night this time as Cheltenham scored all five of those and a save from Stuart O’Keefe’s effort from Gills' second attempt meant the visitors won the contest 5-4. Lee, Danny Lloyd, Carayol and Dan Adshead all scored their spot-kicks for Gills.
Gillingham: Chapman, McKenzie, Ehmer, Bennett, Tutonda (Akehurst 38mins), O'Keefe, Adshead, Lloyd, Reeves (Carayol 76mins), Lee, Oliver (Tucker 46mins). Subs not used: Cumming, Jackson, Phillips, Dempsey.
Cheltenham: Evans, Long (Boyle 46mins), Tozer, Freestone, Sercombe (Wright 60mins), Horton, Perry, Blair, Chapman, Lloyd, May (Thomas 66mins). Subs not used: Flinders, Williams, Bonds.
Referee: David Rock.