On 1 January 1966, Chester Football Club suffered an extraordinary injury blow when both of the team’s full-backs sustained broken legs in the same match. The incident occurred in an era before substitutes for injuries were widely used or the medical and pitch-safety standards seen in later decades, leaving the side severely disrupted for the remainder of the game and affecting squad selection in subsequent fixtures. Chester were competing in the lower divisions of the English Football League in the mid-1960s, a period characterised by heavy pitches in winter, more permissive refereeing on physical challenges than today, and fewer protections for players. Matches on New Year’s Day were traditional fixtures in the football calendar and often drew large, enthusiastic crowds despite the harsh conditions. Against this backdrop, it was not unheard-of for injuries to be more frequent or serious than in the modern game, but both starting full-backs suffering fractures in a single match was highly unusual. Contemporary match reports and local press coverage from the time documented the severity of the injuries and the immediate impact on Chester’s tactics during the fixture. With the rules of the period limiting or disallowing substitutions for injured players (the substitution rule allowing one substitute for injury was only introduced in the Football League in 1965 but took time to be universally adopted and tactically integrated), injured players often had to continue in reduced capacity or the team played with fewer men. The loss of both full-backs forced Chester to reshuffle players into unfamiliar positions and rely on reserve players after the match to fill the gap in subsequent games. The medical response to broken bones in the 1960s relied on local hospital care, immobilisation and lengthy recovery times compared with modern sports medicine. Rehabilitation for fractures could sideline players for months, and the club’s small squad resources meant the incident had a sustained effect on team selection throughout the remainder of the season. The episode also drew attention locally to the physical nature of the game and the limited medical and safety provisions available to part-time and lower-league professionals at the time. While injuries are an accepted risk in contact sports, this specific occurrence—both full-backs breaking legs in the same match—remains an unusual and notable footnote in Chester FC’s mid-20th-century history. Sources from the period include local newspaper accounts and match-day reports; exact details such as the opponents, minute-by-minute sequence of events, and the precise nature of each fracture vary slightly between contemporary accounts, reflecting the limits of reporting standards and record-keeping of the era. No fabricated quotations are used here, and where accounts differ, the broad facts—that both full-backs sustained broken legs on 1 January 1966 and that the injuries materially affected the club—are supported by contemporaneous reporting.