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.
13. SUB 2: Rasmus Nicolaisen
The Danish centre-back played a total of 27 times for Pompey and was an unused sub in Cowley’s first game in charge. He managed to make seven appearances under the new Blues boss before he returned to FC Midtjylland in the summer. Despite playing three times for the Wolves in Europe at the start of the season, the 25-year-old joined Ligue 2 side Toulouse where has played 27 times to date. Photo: Joe Pepler
14. SUB 3: Charlie Daniels
Danies had a tough stay at Fratton Park only managing to play 18 times for Pompey, seven of which came under the new boss. The left-back failed to make a real impact for the Blues and would go on to join League Two side Colchester in the summer, where he has only managed to appear 17 times this term. Photo: Alex Burstow
15. SUB 4: Haji Mnoga
The young defender flirted around the Blues squad for the remainder of last season. Mnoga spent the first part of the current campaign at Bromley where he had an unsuccessful loan spell and returned to Pompey before being sent out to Weymouth in January. Photo: Joe Pepler
16. SUB 5: Ben Close
After a difficult season under Kenny Jackett, the Blues academy graduate played 11 times out of Cowley’s first 12 games in charge. Yet, the midfielder was another player who failed to agree a new deal at Fratton Park and would go on to join Doncaster. Close has had a tough time at the Keepmoat being limited to just 17 games because of an ongoing hamstring injury. Photo: Joe Pepler