Danny Cowley’s men advanced to the third round of the competition after a dominant display saw them defeat their old foes 5-2 at Fratton Park.
Goals from Zak Swanson, Michael Jacobs, a double from Reeco Hackett and a debut strike for academy talent Koby Mottoh completed the rout for the Blues.
Indeed the derby didn’t disappoint, with seven goals and a sending off part of an entertaining tie in the first meeting between the two clubs since 2019.
Although the clash was in very different circumstances to their previous encounter, 2,542 supporters were in attendance at PO4, which also included 285 Reds fans who made the short trip down the M27.
We’ve chosen our 15 favourite photos from the clash which perfectly capture the evening under the lights.
5. Pompey 5-2 Southampton: Hampshire Cup
It was like pin-ball in the Southampton penalty area with the Saints failing to clear. Hackett was there to pounce and he soon doubled Pompey's lead. Photo: Jason Brown
6. Pompey 5-2 Southampton: Hampshire Cup
The stars were out as Pompey eased to victory against their south coast rivals. Photo: Jason Brown
7. Pompey 5-2 Southampton: Hampshire Cup
Pompey fans have called on Danny Cowley to start at Kieron Freeman following their recent defensive issues. The right-back didn't do his cause any harm as he put on another stellar performance in the back-line. Photo: Jason Brown
8. Pompey 5-2 Southampton: Hampshire Cup
Michael Jacobs wriggled his way into the box and capped off the first-half scoring when his effort found the net on 37 minutes. Photo: Jason Brown