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.
9. LM: Ronan Curtis
The winger played 11 times after Cowley’s arrival and managed to find the back of the net four times during those games. Despite attracting interest from the Championship, the Irishman has since struggled to reach the same heights only managing to score on five occasions during 32 appearances this term. Photo: Joe Pepler
10. ST: Ryan Williams
The Australian featured in all 12 games under the former Lincoln manager, while also netting twice in that period. Williams was one of the five men who failed to renegotiate a new contract and departed for Oxford United. The 28-year-old has found life hard at the Kassam only managing to make 19 starts in all competitions this season. Photo: Joe Pepler
11. ST: Jordy Hiwula
The Ipswich victory was the only league start the 27-year-old was given during his year-long stay at Fratton Park. With his only goals coming in the Papa John’s Trophy, he was released and has again found it difficult at his new club Doncaster. The striker made his first appearance in two months in Rovers' 1-0 defeat over Gillingham last Saturday but has only scored once in 23 times this season. Photo: Joe Pepler
12. SUB 1: Lewis Ward
The keeper failed to make an appearance for Pompey during his six-month loan stay at Fratton Park. After being released from Exeter in the summer, he joined Swindon but has had a difficult start to life at the County Ground having to settle to be second choice for regular stopper Jojo Williams. Photo: Jason Brown