Norman Dean first joined Southampton in September 1961 as an amateur with the club's nursery side, CPC Sports, while undertaking a welding apprenticeship. He spent a long time in the club's reserve team, scoring 66 goals in 105 appearances for the reserves. He made his first appearance in the first team in a League Cup tie at Tranmere Rovers on 13 September 1963, but had to wait until September 1965 for his first league appearance.
He was a valuable member of the team, alongside Terry Paine, John Sydenham and Martin Chivers that gained Southampton promotion from League Division 2 in 1965–66, scoring 11 goals in 18 appearances, including a hat-trick against local rivals, Portsmouth on 5 February 1966. After Saints reached Division 1, he was replaced by Ron Davies.[2]
In March 1967, he was signed by Jimmy Scoular for Cardiff City for a fee of £6000.[3] In the rest of the 1966-67 season he was virtually an ever-present, making 10 league appearances, scoring 2 goals. He also helped Cardiff to the Welsh Cup in 1967 and again the following season.
The following season, Dean struggled to establish himself in the first-team but, with Bobby Brown injured and Brian Clark ineligible, Dean featured in the 1967–68 Cup Winners' Cup, scoring 3 goals including the winner in the quarter-final play-off against Moscow Torpedo and 2 goals in the semi-final against Hamburg,[4] which Cardiff lost 4–3 on aggregate.[3]
In September 1968, he moved on to Barnsley where he stayed for 4 years, before a broken leg hastened his retirement.