When Baelfire meets Robin Hood and the Merry Men, he has an idea of how to get to Neverland. By getting Roland to say "I believe", Peter Pan's shadow is summoned. The shadow tries to take Roland away, by ends up taking Baelfire to Neverland.
During the second Dark Curse, where everyone is returned to the Enchanted Forest, a flying monkey attacks Regina, but Roland is also in harm's way. Potentially saving Roland's life, Regina transforms the flying monkey into a toy, which she gives to Roland. Robin Hood becomes very grateful for this. After Snow White unleashes the third Dark Curse, Roland - along with the other Merry Men - are transported to Storybrooke this time. In Storybrooke, Regina eventually trusts Robin Hood enough to give him her heart, due to her and Tinker Bell discovering in the Enchanted Forest that Robin Hood is Regina's destined true love. However, Regina's sister Zelena sends Rumplestiltskin to retrieve the heart, as she needs it for a time-travelling spell. Rumplestiltskin threatens Roland's life, until Robin Hood surrenders the heart over to him.
Roland's mother Marian is revealed to still be alive, driving a wedge between Robin and Regina's relationship. Although Marian eventually concedes to the idea of staying out of the way while they be together, she suffers a lethal spell from Ingrid - who did this in an attempt to frame Elsa - and is forced to leave Storybrooke so that the magic no longer has an effect on her. When she leaves Storybrooke, she is instantly cured, and Regina is willing to let Robin Hood and Roland go with Marian. Roland eventually returns to Storybrooke with his father, after it is discovered that Marian is actually Zelena in disguise.
Roland goes with his father and the other heroes to Camelot, only for them to return to Storybrooke with no memories of their time in Camelot. Roland is eventually orphaned when Robin meets his demise at the hands of Hades, and attends his father's funeral, deeply saddened by the loss of his father. Later, Roland goes with the other Merry Men back to the Enchanted Forest through a portal created by Zelena.
- Roland is the youngest person to be with Robin Hood and the Merry Men.
- S3, E03: "Quite a Common Fairy"
- S3, E13: "Witch Hunt" (flashback)
- S3, E15: "Quiet Minds"
- S3, E18: "Bleeding Through"
- S3, E22: "There's No Place Like Home"
- S4, E01: "A Tale of Two Sisters"
- S4, E03: "Rocky Road"
- S4, E09: "Fall"
- S4, E11: "Heroes and Villains"
- S4, E17: "Heart Of Gold"
- S5, E01: "The Dark Swan"
- S5, E02: "The Price"
- S5, E10: "Broken Heart"
- S5, E21: "Last Rites"
- S5, E22: "Only You"