In 1959, Raymond began an affair with Sylvia Goodwin despite the fact that she had a husband and young son Roy Cropper. While Sylvia's affair was kept secret from her family until her death in January 2019, when Roy found a ring with Raymond's initials engraved, it was common knowledge to Alice and her mother. Despite having forgiven Raymond, mention of Sylvia's name would still bring large conflict between Alice's mother and father until his death in 2006.
In June 2019, Wayne Hayes was able to track Alice down after becoming involved in the mystery of Sylvia's ring - however, Roy wanted nothing more to do with the investigation after discovering his mother's affair. Eventually, following persuasion from Cathy Matthews and Brian Packham, Roy decided to meet with Alice to learn the full truth. Before departing, Alice left some of Sylvia's love letter with Roy before telling him to get in touch if he had anymore questions.
By November 2019, Roy had become aware of the existence of a half-brother Richard (born as a result of Raymond and Sylvia's affair) and regularly competed against him in online tournaments in order to get close to him. When the pair finally met Roy revealed the truth about his identity, but was shocked to discover that Richard was terminally ill and his young daughter Nina was acting as his carer. A month later Richard had passed away.