Robbie arrives in the Square in 1993 with the rest of the Jackson clan. Initially a troublesome teen, Robbie has little success at school and is frequently in trouble for his behaviour, along with his friend Kevin. In November 1994, the pair find a dog which Robbie names Wellard. Robbie manages to persuade the dog's owner to relinquish care to him, after he discovers that Wellard was being neglected, and Wellard then becomes Robbies's pet. As he ages, Robbie becomes more responsible, but has little success in anything he chooses to do. He has several careers in Albert Square including radio control for the Evans' mini cab company, waiter, a job as manager in the local video rental store, and later as the market road sweeper.
Robbie is generally unsuccessful with women. He has a crush on Sarah Hills and is responsible for taking her virginity in 1997. Although Sarah initiated the intercourse, she is unable to cope with what has occurred and runs away, leaving her father Ted Hills to assume that Robbie has raped his daughter. Ted assaults Robbie; he is hospitalised and has to undergo a spleenectomy, before Sarah returns to reveal the truth. Robbie forms a more serious relationship with Kerry Skinner in 2000. They get engaged; however, when Robbie discovers that Kerry has cheated on him, the engagement ends.
Robbie decides to track down his birth father, Gary Bolton in 2001. He finds him in Portsmouth, and discovers he has a half brother, Kevin. The meeting ends up being a disappointment for Robbie, when he discovers Gary had left his own mother to be with his half-brother's mother. He leaves angrily, but Gary later traces Robbie to Walford and gives him a large cheque which allows him to travel around India, and pay for sister Sonia's nursing training. When Robbie returns to Walford and meets young widow Nita Mistry, they begin a slow-burning relationship, despite Nita's initial reticence. Eventually they move in together with Nita's son Anish, but Nita decides to return to India in 2003 to live with her parents, who can provide for Anish better than she can. Robbie goes with her and Anish to live in Mumbai, and he leaves Wellard in the care of his friend, Gus Smith.
Robbie returns briefly for Sonia and Martin Fowler's wedding in 2004. He returns again for Bianca's wedding to Ricky Butcher in February 2010, and is upset to hear that Wellard has died. When asked about Nita, he reveals that she cannot attend the wedding as she is six months pregnant. Robbie walks Bianca down the aisle on her wedding day and returns to India after the wedding. When Robbie's half brother Billie suddenly dies several months later, Robbie, Nita and Sonia are unable to attend his funeral due to the flight costs, their newborn baby and the fact that Sonia is visiting Robbie and Nita in Mumbai.
In 2017, Robbie returned to Walford again, having been made a market inspector. His friend Martin Fowler was dubious about this but Robbie said he is qualified. Robbie evicted Donna Yates from her pitch as she was late in rent arrears. Robbie started throwing his weight around a bit so Martin and Kush Kazemi threw Robbie in a rubbish bin.