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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.
5. Centre-back: Sean Raggett
After initially arriving on loan from Norwich in 2019, the centre-back left Fratton Park as cult hero. The popular defender amassed 239 appearances and scored 17 goals during a five-year stay on the south coast - playing a key role under both Cowley and Mousinho. The 31-year-old lifted the League One trophy with the Blues last term before being released after Pompey made the step-up to the Championship. Raggett joined Rotherham last summer but has struggled with injuries, which has reduced him to 11 appearances this season. | National World
6. Left-back: Lee Brown
The popular left-back remained through the mass-exoduse under Cowley that summer, but departed Fratton Park in January 2022 to join AFC Wimbledon. After struggling to combine a playing career with his booming multi-million pound business, Brown retired from the game in 2024 to focus on B3 Homes, which he formed in 2018. The 34-year-old now has a portfolio of luxury homes, which sell on average for £1.25m each. | PinPep Media / Joe Pepler
7. Right midfield: Marcus Harness
The winger netted the second goal of the Cowley era at Fratton Park, when he scored the second-half winner against the Tractor Boys. Harness moved to Ipswich in 2023 and won back-to-back promotions at Portman Road before departing East Anglia following their step up to the Premier League. The 29-year-old joined Derby on a season-long loan and is in battle with Pompey amid a tight Championship relegation battle. | PinPep Media / Joe Pepler
8. Centre midfield: Andy Cannon
Cannon featured 17 times under Cowley during the second half of the 2020-21 campaign but was released by the Blues at the end of the season. The midfielder went on to join newly-promoted Hull in the Championship before dropping to the National League with Stockport just six-months later. The 29-year-old remained in non-league where he made the move to Wrexham and has since helped Phil Parkinson’s men achieve back-to-back promotions to League One. Photo: Joe Pepler