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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.
9. Danny Cowley's first match
March 20 represents Cowley's first game in charge of Pompey four years ago. | PinPep Media / Joe Pepler
10. Centre midfield: Tom Naylor
Naylor netted the opening goal of the Cowley era, when his first-half header levelled the game against Ipswich. Although the Blues captain was offered a new deal - it was on reduced terms and he went on to join Wigan along with fellow team-mate Whatmough. The midfielder dropped to the National League in 2023 to link up with Paul Cook and Chesterfield where he played a key role in their promotion to League Two last season. The 33-year-old has amassed 37 appearances for the Spireits this term. Photo: Joe Pepler
11. Left midfield: Ronan Curtis
The influential winger assisted both goals against Ipswich in Cowley’s first game and that laid the foundations for the Irishman’s influence under the head coach. Curtis remained an ever-present figure in the squad until the Blues boss’ sacking in January 2023. After suffering a season-ending ACL injury a month later, the winger turned down a new deal at PO4 that summer to pursue other options. The 28-year-old is currently operating with Port Vale in League Two and has scored seven goals in 38 games in all competitions to date. Photo: Jason Brown
12. Striker: Ryan Williams
Williams played in an unnatural role in attack against the Tractor Boys, with both John Marquis and Ellis Harrison absent for the game. The winger was released by Pompey that summer before he joined League One rivals Oxford United. His stint at the Kassam Stadium would only last 12-months however, and later returned to Australia to join Perth Glory. A move to the Indian first-tier followed in 2023 - joining Bengaluru on a two-year deal. The 31-year-old has netted six goals and registered four assists in the Indian Super League this season. | Getty Images