Julen Lopetegui’s first game in charge was not quite the same as his side struggled to break down the bottom-placed club in League Two.
With frustration mounting, Wolves finally won a penalty and needed returning striker Jimenez, who had not played since 31 August due to injury, to score it in the 77th minute.
Then Riane Ait Nuri scored a second late on, to send the Wolves through to the next round.
Wolves dominated possession from the start and created the first opening. A two-pass pass between Hugo Bueno and Joao Moutinho saw the former shoot, but goalkeeper Jake Turner was equal to it.
Then Bueno delivered a fine shot from the left, Diego Costa lurking, but Gillingham cleared their lines.
After the opening 10 minutes, Wolves were almost exclusively in Gillingham’s half but they were unable to create any clear chances, while the visitors were pleased with the clock ticking down – prompting Lopetegui to complain to the fourth official about wasting time.
Bueno was the pick of the Wolves pack in the opening stages and again nearly set up the first goal with another tidy run off the left. Costa nearly met his cross, before Joe Hodge caught a bump.
Costa had half a chance when Daniel Bodence met a ball over the top. He tried to push her back towards the goal, but he directed her away.
Gillingham had a chance when they eventually took the lead and won a corner. The scramble into the wolves’ chest frightened everyone, but they removed the danger with the skin of their teeth.
Ruben Neves then approached with a free kick from 25 yards which went wide of the post.
Although frustrations were running high inside Molineux, Wolves put in a superb passing display which saw a shot from Costa put Moutinho on goal, only for the ball to escape him when he was to have a free kick from 10 yards out.
Moments later, Costa was about to go in but had to stretch for the ball, and Turner collected it.
Wolves started to pile on the pressure in the closing minutes of the first half. A deceptive shot from range by Bodence was saved by Turner but it spilled in the penalty area, and Costa was beaten by a defender.
With that opening goal still elusive, Hodge had to find it. He had a five-yard free header after Goncalo Guedes’ cross, but headed wide.
Haseeb Adelakon had an optimistic long-distance effort for Gillingham, which was high and wide, in one of his few attacks.
The final kick of the ball before half-time saw Neves hit the post with a shot from distance.
Wolves entered the first half tied 0-0 after a agonizing 45 minutes as they dominated possession, but could do little.
With the teams coming into the second half, Adama Traore replaced Hodge, meaning a change in the formation to 4-2-3-1. Bodence moved on to play behind Costa.
In the opening stages from the 45th second, Gillingham was more pleased by hitting the ball forward to striker Mickael Mandron. He was doing a good job of lifting the ball and winning the header, as the visitors looked to hurt Wolves with set-pieces.
If the first half was painful, the second half was even more painful as the match exceeded the 60 minute mark. The Wolves were unable to inject any urgency and life into the match, as the crowd became increasingly frustrated.
Trying to turn around their fortunes, Wolves introduced Mateus Nunes and Hwang Hee-chan, replacing Moutinho and Guedes.
Costa, who had done very little on the night, came close when he hit a shot just wide. The striker then received support up front when Jimenez replaced Bodens, making his first appearance since August 31.
The pair linked up immediately and Costa’s sweet flick almost gave Jimenez a good chance, but he closed in just inside the penalty area. Soon after, Jiménez nodded from a corner.
Then a great opportunity fell for the Wolves. Nunes’ ball found Nelson Semedo and his shot was saved – and from the resulting corner, Wolves won a penalty.
Cheye Alexander took down Hwang and immediately gave Jimenez a shot, which he expertly dispatched.
Ait Nouri finished off an impressive attacking run in injury time to give Wolves a second, in a record that earned their performance praise.
Hwang missed a great chance with a shot over the keeper at the death as Wolves secured a place in the quarter-finals on Thursday.
45 Chance Neves hits the post with a halftime kick
77 Jimenez’s goal gives Wolverhampton the lead from a penalty kick
90 Ait Nouri’s goal finishes a nice move
Wolves: Sa, Semedo, Collins, Kilman, Bueno, Hodge (45), Neves, Moutinho (Nunes, 60), Guedes (Hwang, 60), Costa (Ait-Nouri, 81), Podence (Jimenez, 67). ..
Unused subs: Sarkić, Lempicka, Gomez, Ronan.
Gillingham: Turner, Alexander, Totonda, Wright, Ehmer, Williams (Lee, 73), O’Keeffe (Reeves, 73), Mandon (Cashkett, 64), Jeffries (McDonald, 73), Adelacon, Bagot.
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