Dewar's actions off the field overshadowed his performance on the field during his early spell at the club; he had eloped with the daughter of Manchester United director councillor A. E. Thompson. The couple eventually married in a registry office but the scandal surrounding the affair led to the resignation of Thompson from the United board. A few months later, during Dewar's first season in Sheffield, the couple had a child, Neil junior, who also went on to become a footballer, playing for Altrincham.