Doug Loft secured a morale-boosting win for ten-man Gillingham in the Johnstone’s Paint area quarter-final.
The Gills came from a goal behind, after Izale McLeod put the hosts ahead from the penalty spot, with two second half goals.
Gillingham’s hopes were dented when Joe Martin was dismissed for an off-the-ball incident with McLeod in the second half.
Despite the set-back the Gills levelled through Jermaine McGlashan and won it with a late Loft effort.
Gillingham had gone six games without a win. Their last success came in the same competition, beating Colchester on penalties. Just one win in normal time had come their way in 13.
Boss Peter Taylor named a reasonably strong team for the match. There was no Cody McDonald for the Gills, who was rested, while defender Kortney Hause was missing on international duty for England under-20s.
Both Taylor and home manager John Gregory were desperate for a win. Both had slipped down the League 1 table and both suffered FA Cup defeats at the weekend.
Gillingham had several half chances in the opening 45 minutes but failed to work the home keeper Jamie Ashdown.
John Egan headed a chance over and German shot wide but it was Norris who came closest for the visitors. He teed up a chance for himself in the box but the resulting drive, on the spin, was blasted wide.
Gills keeper Stuart Nelson had been the busier of the two keepers, making saves from Jimmy Smith and former Gills forward Gavin Tomlin.
Nelson – the penalty hero during the last JPT game – was beaten from the spot in the first half. Jake Hessenthaler fouled Gwion Edwards in the box and McLeod rolled the ball home from the spot.
Taylor made a double sub at the break with Jermaine McGlashan and Bradley Dack joining the action. Hessenthaler reverted to right-back.
McGlashan’s pace won the Gills an early free-kick and a corner but neither were capitalised on. Skipper Doug Loft volleyed an effort just past the hour, moments before the Gills went down to 10 men.
Martin went head to head with McLeod and raised a hand. Referee Darren Sheldrake, who had sent off six players already this season, made it seven with a red for the Gills left-back.
Gillingham survived a few scares before McGlashan drilled in a low shot to beat Ashdown in the Crawley goal.
McGlashan missed a great chance to put Gills ahead. He slid onto a Dack cross and from just a few yards out he put the chance over. Dickenson also shot wide as the Gills looked more dangerous with 10 men than 11.
With two minutes left Loft whipped in a cross from the wing and it bounced over Ashdown into the net.
Gillingham: Nelson, Fish (Dack 46mins), Martin, Egan, Legge, Loft, Hessenthaler, German (Kedwell 75mins), Norris (McGlashan 46mins), Doughty, Dickenson. Subs not used: G Morris, Hoyte.
Crawley Town: Ashdown, Oyebanjo (Banya 84mins), Dickson (Sadler 54mins), Bradley, Edwards, Smith, Walsh, Keane, Bawling, Tomlin (Young 61mins), McLeod. Subs not used: Jensen, Henderson.
Attendance: 1,305 (310 Gills)