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Gillingham had senior players involved for their Kent Senior Cup match at Tonbridge Angels but fell at the first hurdle in the competition.
The second rounf match at the Longmead Stadium - Gills got a bye in round one - ended 1-1 but Jay Saunders’ non-league side won the subsequent shootout to claim their place in the quarter-finals.
Gills boss Neil Harris was keen to progress in the competition and named a strong side which included a handful of senior players.
Jake Turner was in goal, Cheye Alexander started in defence and there was a place in the side for Jordan Green - having been told he has not future at the club.
New Gillingham signings Ethan Coleman and Jayden Clarke also started, making their first senior appearance for the club following their January transfer moves.
Despite Gills’ competitive line-up, it was Saunders’ side who took an early lead through Tommie Fagg, scoring with just three minutes gone.
Youth striker Joe Gbode was in action for the Gills and was denied by home keeper Jon Henly - who picked up the man-of-the-match award.
Four minutes after the restart Tonbridge were awarded a penalty but Gills keeper Turner saved from Devonte Aransibia.
Gillingham newcomer Clarke - who joined from Dulwich Hamlet - levelled the score with a composed finish after being assisted by Gbode with 77 minutes on the clock
The match ended 1-1 after normal time and went straight to penalties where Tonbridge won the shootout 4-1 after Gillingham had a penalty saved and also missed
Gillingham: Turner, Alexander, Akehurst, Kuhr, Carter, Gale, Green, Coleman, Skipper, Clarke, Gbode. Subs: Giles, Holtam, Bayliss, Garrett, Bridle. Attendance: 452.