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Gillingham 1-1 Coventry - Gills score late equaliser from spot before shootout success
Coventry City were knocked out of the Carabao Cup by Gillingham on penalties after a sensational late twist at the Priestfield Stadium.
Coventry sub Max Biamou looked to have struck the only goal of the game on 61 minutes just after coming on.
But Jordan Graham netted from the spot in injury time after Michael Rose was adjudged to have felled Vadaine Oliver.
Rose then blazed City's fourth penalty in the shootout over, but Steve Evans' Gills converted all five to win 5-4.
Trae Coyle struck the winning shootout penalty to earn a third-round trip to either Wolves or Stoke.
But the game was marred by a serious first-half injury to stand-in Gills captain Stuart O'Keefe, who has a suspected broken ankle.
Both sides made major changes after each opened the EFL season on Saturday with defeats. Gillingham made six alterations from their 2-0 home defeat by Hull City, while promoted Championship new boys Coventry changed their entire team from the 2-1 loss at Bristol City.
Coventry always looked the more dominant side, taking a deserved lead just four minutes after Biamou had come on as a 57th-minute substitute, after good work by Brandon Mason.
But when they failed to defend a 94th-minute swinging cross from the right, Oliver crashed to the floor and referee Craig Hicks pointed to the spot.
Tyler Walker, who had earlier hit the post in the first half, Biamou and Ben Sheaf all scored for Coventry in the shootout, matched by successful penalties for Connor Ogilvie, Graham and Scott Robertson.
But, at 3-3, Rose missed and, although Josh Eccles converted City's final penalty, Jacob Mellis and Coyle both kept their nerve.
Gillingham manager Steve Evans:
"We had to find a way to stay in the game. It's a good result for us but the performance was scrappy.
"They've missed a couple of good chances in the first half. They should have comfortably been in front. But we've done that before and you can pay the price for it.
"The initial assessment is that it is a broken ankle for Stuart. It's a naughty challenge - I thought that at the time and looking back at it on the screen it really is naughty.
"In all fairness that kid [Amadou Bakayoko] isn't normally like that but it's an horrendous challenge. I don't look at the player. I look at the referee and why he didn't take the appropriate action."
Coventry City manager Mark Robins:
"There's a lot of pleasing aspects but I'm disappointed to lose the shoot-out. When you get to that point, and it shouldn't have got to that point, it's a lottery.
"I haven't seen the penalty incident back but everybody's telling me that it's harsh. It's really just hands on each other and their player has gone to the ground pretty easily.
"But that's what happens if you give the referee a decision to make. It's really disappointing as they never really threatened anything."