The Blues boss was victorious that day in the Fratton Park dugout as his newly-inherited squad came from behind to snatch all three points from Paul Cook’s Ipswich.
A 32nd-minute James Norwood strike put the visitors ahead, before goals from Tom Naylor and Marcus Harness saw Pompey snatch victory.
After replacing Kenny Jackett in March, Cowley would manage the final 12 games of last term, narrowly missing out on the play-offs on the final day.
A summer of transition was soon to follow and only four members of the Blues’ current team featured in his first match in charge.
We take a look at the first squad Cowley named in his maiden game at the helm at Fratton Park and what those players have gone on to do since.
5. LB: Lee Brown
The 31-year-old missed a large chunk of the action towards the end of last term after sustaining a hamstring injury against Burton. Cowley opted to continue with the left-back into this campaign but failed to adjust to the new wing-back role. Brown joined AFC Wimbledon in January where he has played 10 times for the Wombles since his arrival. Photo: Joe Pepler
6. RM: Marcus Harness
Harness netted what would be the winner against Ipswich and was challenged by Cowley to go on a string goal scoring run. He would only find the back of the net once more last term but has played a crucial part in the Blues’ attacking threat scoring 11 times this season. Photo: Joe Pepler
7. CM: Tom Naylor
Another goal scorer on the day against Ipswich and the skipper played every game under Cowley before the summer. However, the 30-year-old would be another member of the squad to fail to agree to a new deal at Fratton Park and linked up with Whatmough at Wigan. Despite not reaching the same goal scoring heights like his final season at Pompey, Naylor has featured 37 times for the Latics this campaign as they bid for promotion. Photo: Joe Pepler
8. CM: Andy Cannon
Cannon played 10 times in total under the new boss but was released following the expiration of his contract. He joined newly promoted Hull in the Championship and scored on his debut against Preston, but the 26-year-old has had a tough time at the Tigers only managing 11 appearances due to an ankle ligament injury. Photo: Joe Pepler