Although it may not have seemed it at the time, the 2-0 defeat at Preston sparked an incredible journey for the ex-West Ham boss in charge of the Blues.
Promotion to the Premier League, consecutive top-nine finishes, an FA Cup triumph, and a first European campaign were all achieved under his stewardship – across two spells.
Here’s what we’ve selected as the 75-year-old’s greatest matches as Fratton chief.
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5. Pompey 4-0 Bolton (26-06-2003)
Pompey climbed to the top of the Premier League with a resounding win over Bolton at Fratton Park. A second-half hat-trick from Teddy Sheringham proved their was still life in the old dog, yet, after Steve Stone had put the hosts ahead. Picture: Jamie McDonald/Getty Images
Photo: Jamie McDonald
6. Pompey 1-0 Southampton (21-03-2004)
Pompey secured their first home victory against that lot up the road since the 1960s when Yakubu's goal settled a scrappy affair. The striker had fired home Stone's cross to send the home fans into raptures, with some entering the pitch. Nerves were heightened when Kevin Phillips hit the post for Saints in injury time, before the three points also kept alive the club's survival hopes. Picture: Mike Egerton
Photo: Mike Egerton
7. Pompey 1-0 Manchester United (17-04-2004)
Redknapp's side strengthened their survival bid by recording a memorable victory over Sir Alex Ferguson's Manchester United dynasty. Stone's powerful effort following a neat Yakubu touch was enough to edge the Red Devils. Picture: Mike Egerton
Photo: Mike Egerton
8. Pompey 2-1 Manchester City (11-03-2006)
Pedro Mendes' dramatic brace ignited Pompey's great escape from relegation following Redknapp's return from arch-rivals Southampton. The Fratton faithful were fearing the worst when the visitors equalised following the midfielder's first jaw-dropping effort. However, deep into injury time, he repeated the trick by slamming the ball into the top corner from the edge of the box to claim three vital points.
Photo: XX