Legend has it that Herbert Munday joined Chesterfield Town as an afterthought on the part of Paul Cutts, who asked to bring a friend along when he joined the club in the summer of 1893. Herbert had been keen on football from his earliest years, but this enthusiasm was not shared by his first employer, a pawnbroker, so he quit the comfortable life in a shop and took a job in the stables at Renishaw Colliery, in order to be able to play. Despite his rather frail appearance, and his inability to do anything with his right foot beyond standing on it, he quickly began to establish a name for himself, and he was selected to represent the Sheffield FA against the London FA in October, 1893.

Herbert came as a left-winger but moved to the inside-left position at the start of his second season. He scored at a consistent, if unspectacular, rate, and began to attract the attentions of Football League scouts. After three years, he had scored 35 goals in 75 Sheffield League appearances and made an effortless switch to Midland League football. Another three seasons of that brought 53 goals in 71 games. In April 1898 he was awarded a benefit, against Long Eaton Rangers. The town turned out in some numbers to acclaim the man who was, by now, the greatest player in Town's short history.

When the club made their Football League bow, Herbert scored their first goal which, for a while, looked like spoiling the opening-day celebrations at Sheffield Wednesday's new Hillsborough ground. He continued to score regularly throughout the Town club's time in the League, and turned down offers from almost every other League club in that time. Defenders often found desperate ways of stopping him: he received broken fingers when someone stamped on his hand, and was once kicked over the eye while standing. He was selected to play for the Football League against the Irish League at Belfast in 1904, and was awarded a second benefit a year later.

In 1908 he began playing at left-half, using his skill, guile and experience to service the forwards as advancing years and regular kickings took their toll on his pace. This positional change extended Herbert's period of service into its eighteenth year, playing through two seasons of Midland League football before saying farewell to the club in 1911, after a third benefit match. A social gathering was held at the Rutland Hotel in May to allow the club and its closest supporters to say "Cheerio" in an informal manner and to present Herbert with a benefit cheque for over £160. This works out to around £12,000 at 2012 prices - not bad, for a whip-round! One question was asked of him more than any other, that night: about his unbending loyalty to the Chesterfield Town Football Club.  Talking of a career which had occupied more than half his life, he offered a typically straightforward explanation for his astounding loyalty: "The good feeling extended to me as a lad has been handed down from one management to another... and that has been one of the main reasons of my stopping here."

Herbert retired to his native Eckington and became 'mine host' at the Rose and Crown, while turning out for the pub's team. They won every match in 1911-12. A 1920 biography in a local paper spoke of his having returned to mining, while being a keen cricketer, fisherman and follower of hounds. He became an occasional visitor to Saltergate, receiving standing ovations for many years after his retirement. Herbert's son Harold signed for Chesterfield in the 1920s, but made no impression on the first team.

For Chesterfield Town: 314 Football League appearances, 107 goals.