Maddy was an instant hit with everyone upon her arrival in Erinsborough. Everyone, that is, except her father, who struggled to deal with the revelation that Lori hadn’t gone through with the termination after all. At first, Connor found it difficult to spend time with his daughter, while Lori’s ex, Jack Scully, soon bonded with her. As Connor then started to relax into the role of father, Lori found herself with two men fighting over what was best for her and Maddy. When Jack offered her a fresh start with him, she happily accepted, since she’d never really stopped loving him. However, Maddy’s welfare had to come first, and when Jack’s mother, Lyn, made it quite clear that Jack would probably get bored quite quickly and want to move on, Lori decided that she had to be independent. Lori accepted a job at a salon in Lorne, a couple of hours away from Melbourne. Connor told his daughter that he would always be there for her, no matter what happened and Lori and Maddy left Erinsborough for a new start together.

A few months later, Maddy went to stay with her dad in Ramsay Street for a few days, while Lori was in Sydney for a fashion show. Connor took his responsibilities to her very seriously, and the women of Ramsay Street couldn’t help but love the little girl. However, Connor's housemate, Toadie wasn’t quite so quick to fall under her spell, admitting that he couldn’t stand babies. Meanwhile, Connor struggled to cope with running the pub while Lou was in prison, as well as looking after his daughter. When Stingray called over one day, he noticed how busy Connor was, and, as Connor turned his back for only a moment, Stingray took the baby out in her pram, thinking it would help. Maddy was taken for a walk in the park, but Stingray got distracted by some of his skater friends, and a couple saw the pram and thought the baby had been abandoned. Stingray panicked and called the police, with Stuart turning up some time later. With several Ramsay Street residents out looking, Maddy was finally found by Stuart and returned to his father. However, Lori was furious when she heard what had happened and demanded that Maddy be taken home immediately, leaving Connor to worry about whether he would ever be trusted with his own daughter again.

The regular visits continued over the months that followed and everything settled back into a regular pattern for Connor and Maddy. Then Lori met Nick Sullivan, who she started dating and Maddy seemed to have two father figures in her life. The situation got awkward one afternoon when Connor arrived at Nick’s house to collect Maddy. Nick’s family were there for a party and he told Connor that Maddy was happily playing and he’d rather not disturb her. Connor accepted this, until his girlfriend, Carmella Cammeniti, convinced him that he had a right to spend time with his daughter. Another confrontation followed and Lori was forced to step in. She turned up in Ramsay Street later that week and broke the news to Connor that she, Nick and Maddy would be moving to Adelaide.

Desperate to still have regular access to Maddy, Connor became depressed at the thought of his daughter growing up believing that Nick was her father. When Lori and Nick returned to town later that week, to collect Maddy, Connor finally snapped. As he saw them loading up their car outside Lassiter’s Hotel, and Nick left Maddy alone in her stroller for a few seconds, he snatched his own daughter. Fortunately, the incident made Lori realise just how painful it would be to separate father and daughter and she announced that she would be staying in the area. Nick was appalled and Lori told him that he obviously had his own best interests at heart, so she no longer wanted to see him. Following this, Lori allowed Connor even more time with Maddy, and they managed to spend Christmas Eve together.

Several months later, Maddy was diagnosed with a serious ear infection, requiring an operation, and it was left to Connor to try to raise the $50,000 required. Fortunately, he managed to borrow the money from Carmella's mother and the operation took place.