The former Lincoln and Huddersfield boss was the man chosen to succeed Kenny Jackett at Fratton Park, after being sacked following defeat to Salford in the EFL Trophy final at Wembley.
After being appointed on a deal until the end of the campaign on March 19, the Blues head coach went straight to work as Pompey welcomed Paul Cook’s Ipswich a day later.
His new side were on a disappointing run of form, having won one of their previous eight league games and crucially sliding away from the automatic promotion picture.
But a surprise 2-1 win over the Tractor Boys set a positive tone to Cowley’s era on the south coast, with Tom Naylor and Marcus Harness doing the damage.
Four years later, a lot has changed at Fratton Park with the Blues operating in the Championship under John Mousinho and a completely new squad compared to that seen in the 46-year-old’s first game in charge.
But who featured on March 20 against Ipswich and where are they now? Find out below to see who started in the 46-year-old’s maiden fixture in the hot seat.
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1. Where is the Pompey squad from Danny Cowley's first game in charge?
Where is the Pompey squad from Danny Cowley's first game in charge? | PinPep Media / Joe Pepler
2. Goalkeeper: Craig MacGillivray
The shot stopper cemented his place as first-choice keeper earlier in the campaign under Jackett and remained number one with Cowley in charge. After departing Fratton Park that summer, the former Scotland international joined Charlton before spells at Burton, MK Dons and Stevenage. The 32-year-old has made just five appearances in League Two at Stadium MK but is behind Connal Trueman in the pecking order. Photo: Joe Pepler
3. Right-back: James Bolton
The right-back wasn't promised regular game time under Cowley, which prompted a summer switch to Plymouth for an undisclosed fee. Bolton would be frustrated again, though, this time through injury as ankle issues blighted his two-year stay at Home Park. The 30-year-old is now operating in League Two with Fleetwood, where he has made 33 appearances in all competitions following a move from St Mirren in July 2024. Photo: Naomi Baker
4. Centre-back: Jack Whatmough
The Fratton Park academy graduate started Cowley’s first game in charge and was a prominent figure in the Blues' backline during the second-half of the campaign. However, the centre-back departed PO4 that summer to link-up with former Pompey coach Leam Richardson at Wigan. Whatmough made the move to rivals Preston in 2023 and remains at Deepdale but will miss the rest half of the Championship season with a calf injury. | PinPep Media / Joe Pepler