Crawley Town suffered their first home defeat since Gabriele Cioffi took charge when they lost 1-0 to Portsmouth in the Checkatrade Trophy.
A 37th minute goal by Pompey’s Dion Donahue settled the result of Reds’ second outing in the competition this season.
Portsmouth missed a golden chance to extend their lead at the end of the game when Joe Mason skied a penalty kick well over the bar.
Gabriele Cioffi made ten changes to the side which beat Cambridge United 2-0 on Saturday.
A trio of Crawley players made their first starts for the club: David Sesay, Brian Galach and Tarryn Allarakhia.
Only Dominic Poleon remained from the starting XI with goalkeeper Yusuf Mersin, Josh Doherty, George Francomb, David Sesey, Romain Vincelot, Brian Galach, Tarryn Allarakhia, Panutche Camara all coming into the side along with Dannie Bulman who was wearing the captain’s armband.
Portsmouth made nine changes with captain Gareth Evans and Ben Close surviving from Saturday.
Manager Kenny Jackett handed a debut to 16-year-old full-back Hagi Mnoga.
The only early chance of note was a shot by Pompey’s Louis Dennis from 25 yards which flew wide of the post.
A quiet first half sprang into action when Portsmouth took the lead in the 37th minute.
Evans and Joe Mason combined to supply Dion Donohue who cut inside from the left and fired past Mersin.
Portsmouth made a substitution at half-time with Matt Clarke replacing captain Gareth Evans as they switched to three at the back to match Crawley.
Sesay beat Donohue down the right and squared for an unmarked Galach, who side-footed his shot wide.
Crawley made two substitutions around the hour mark with Joe Maguire replacing Brian Galach and Mark Randall coming on for Camara.
Reds went agonisingly close when Allakrakhia found Doherty on the left whose cross rolled inches away from the line as it ran across the goal.
Portsmouth’s fans were in good cheer, numbering almost 500 they sang throughout and helped create a great atmosphere at the visitors’ end of the ground.
Allarakhia let rip a thumping shot from 25 yards which almost put Reds back on level terms but flew narrowly wide of the post.
Portsmouth should have made in 2-0 in the 88th minute after Randall brought down Anton Walkes but Mason blazed the ensuing spot-kick miles over the crossbar.
Crawley Town: Mersin, Doherty, McNerney, Poleon, Francomb, Sesay, Vincelot, Bulman (capt), Galach (Maguire 57), Allarakhia, Camara (Randall 60)
Unused subs: Morris, Young, Connolly, Payne
Portsmouth (4-2-3-1): McGee, Mnoga (Naylor 65), Burgess, Walkes, Haunstrup, Evans (capt) (Clarke 46), Close, Rose, Donohue (Thompson 64), Dennis, Mason
Unused subs: MacGillivray, Read, Pitman, Hawkins,
Referee: Tim Robinson
Attendance: 1,268 (away 484)
Man of the Match: David Sesay