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.
17. SUB 6: George Byers
The midfielder had a troubled loan spell at Pompey and was an unused sub for Cowley’s first game. He returned to Swansea after making eight appearances under the new Blues boss and would later join Sheffield Wednesday. The 25-year-old has found the net five times in 17 appearances for the Owls this season, although game time has come at a premium. Photo: Joe Pepler
18. SUB 7: Michael Jacobs
Despite coming on as a late sub against Ipswch, the 30-year-old would only play three more times for the Blues in the campaign due to a knee injury. And game time has come at a premium this term due to further injuries yet he has been one of Pompey’s bright sparks - scoring six times in 23 games to date. Photo: Joe Pepler