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.
13. Pompey 5-2 Southampton: Hampshire Cup
Mottoh's academy team-mates surround him after his maiden Blues strike. Photo: Jason Brown
14. Pompey 5-2 Southampton: Hampshire Cup
All smiles at the full-time whistle. Dan Murray and Brian Quarm both featured in the win, which included six academy talents. Photo: Jason Brown
15. Pompey 5-2 Southampton: Hampshire Cup
That's definitely one proud dad. A heart-warming moment when Mottoh was spotted celebrating his first Pompey goal with his father at the full-time whistle. One for the future Pompey fans! Photo: Jason Brown