The midfielder made his Fratton Park return on Wednesday evening after leaving Steve Morrison’s side at the end of last season.
Now the 31-year-old is set to face his former side as soon as Wednesday, August 10, with Danny Cowley’s side due to travel to the Cardiff City Stadium.
Pompey last travelled to the Welsh capital in 2017 when Kenny Jackett’s side took the Bluebirds to extra-time in the first round of the same competition.
The winners of the tie will then play the second round on Wednesday August 27.
First round draw southern section: Norwich v Birmingham, Coventry v Bristol City, Northampton v Wycombe, Charlton v QPR, Crawley v Bristol Rovers, Walsall v Swindon, Ipswich v Colchester, Luton v Newport, Reading v Stevenage, Plymouth v Peterborough, AFC Wimbledon v Gillingham, Cheltenham v Exeter, MK Dons v Sutton, Forest Green v Leyton Orient, Cambridge v Millwall, Oxford United v Swansea.