An outside-left of great distinction, Harold Roberts was skilful, intelligent and, above all, fast, with an excellent pin-point cross. Having had a season at Goodison Park as a sixteen year-old, he joined the Spireites from the Birkenhead-based Harroby FC only weeks before the outbreak of war, and had to wait until hostilities came to an end for his League debut.
Some three and a half years of that wait were spent in a prisoner of war camp in Bremen, following his capture during a Commando raid, "Operation Chariot," on the French port of St. Nazaire. He was reportedly badly wounded in the raid, and was able to resume a football career thanks only to the skill of a German surgeon. The raid would later be immortalised in the 1952 Trevor Howard film. “The Gift Horse.” The experience of capture and imprisonment was character-forming, to say the least: Harold came home harder, and was rarely, if ever, unsettled by the sort of rough play that agricultural full-backs reserved for players of his ability.
Upon his return to Chesterfield Harold lodged with Joe
Spence's family. Spence, the former Chesterfield player and coach, took great
trouble to help Harold recover his fitness and confidence. Happily, he regained
his strength and pace, played for the FA against the Army at Ipswich in 1948
and took his place in what remains the most successful side in Chesterfield's
history, as far as League placings are concerned, until Birmingham came in with
what constituted a record for a fee received by the Spireites, offering
His St Andrew's days were cut short by cartilage and knee ligament damage which dogged the rest of his career. He joined Shrewsbury Town as they made their Football League debut in 1951 and wound down his Football League career at Scunthorpe in 1953, before spells in the non-league game at Matlock Town, Gresley Rovers and Burton Albion. Harold's son, Peter, played for Chesterfield during the early 1970s.
Harold spent eight years during the sixties as a youth worker at the Staveley Youth Club. Towards the end of that decade he joined Chesterfield's coaching staff, assisting Reg Wright with the juniors. The team enjoyed some success, and Harold earned and retained the respect of his young charges. He remained at the club until the financial crisis of 1983, when he and his coaching colleagues were sacked as an economy measure by the new board. The rather abrupt circumstances of the end of his association with Chesterfield FC upset many long-standing supporters but Harold evidently felt no bitterness, and continued to attend matches to offer the club his support, right up to his death in 2007, at the age of 87.
For Chesterfield: 92 FL appearances, 9 goals.