Seeking to double his $7,000 salary from the previous season, Henderson became embroiled in a contract dispute with the Red Wings prior to the 1966–67 NHL season, before the team acceded to his demands. He then spent the year attempting to overcome injuries; a case of tracheitis forced him to miss several early season games and led the team to consider having him play wearing a surgical mask to protect against the cold air of the arena. Henderson eventually spent time in the dry air of Arizona to cure the ailment, but he also suffered from torn chest muscles and ultimately missed a third of the season. On the ice, Henderson scored 21 goals and 40 points in 49 games.