In the 1950-51 season Wednesday had been relegated in their first season back in the First Division. In the Second Division, they struggled at the start of the 1951-52 campaign, winning only three of their opening 11 games. Derek had been on Wednesday’ s books for four years and whilst scoring regularly in the reserves, on the two occasions he’ d been selected for the first team he’ d failed to impress. He was recalled for a league game against Barnsley in October 1951 and he took his opportunity, scoring both Wednesday goals in a 2-1 victory. From then on his place in the team was assured and Derek went on a goalscoring spree, the likes of which the fans had never seen. In just 31 games he scored an incredible 47 goals, included in his six hat-tricks that season were five goals against Notts County and four against both Everton and Cardiff City. Wednesday finished the season as Second Division champions.
After the end of his playing career, Dooley had maintained his contacts with the club and had helped in training the juniors. In 1962, he again became a fulltime employee, when the club set up the Development Fund and chose Dooley as its organiser. When Danny Williams was sacked in January 1971, Dooley was offered the job as manager. For Derek the offer was irresistible and he once again found himself centre-stage.
Dooley stayed in the job for almost three years, during this time he helped restore the dressing room spirit and strengthened the squad with some good signings. The 1972-73 season started well for Wednesday and they were league leaders during the early stages. In the FA Cup they had a splendid Fourth Round victory over First Division Crystal Palace but unfortunately they failed to maintain the momentum and finished in 10th place.
The 1973-74 season did not start well, Wednesday won only two of their first seven games and then a virus infection struck the club, affecting 16 players and Dooley himself. The effects of the virus lasted for over two months from the beginning of September. Dooley struggled to raise a team and was forced to play a combination of untried youngsters and half-fit first-teamers which led to a sequence of results that left Wednesday firmly at the foot of the table. Once again the supporters became restless and in early December, chairman Andrew Stephen (who had been responsible for appointing Dooley) resigned. In a newly constituted board, Matt Sheppard was the chairman. Less than a fortnight later, in a decision which was heartless even by football’ s standards, Dooley was sacked on Christmas Eve.
Understandably, Dooley left the club with feelings of bitterness and it was only as recently as 1994 that he returned to Hillsborough for a Wednesday match. After leaving Wednesday, he eventually joined Sheffield United as their commercial manager. he progressed to become first, a director of the club and eventually the managing director. He kept that position until his retirement in 1994.
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