The chipped cup is Rumplestiltskin's most prized possession in Once Upon a Time, as a memento of his true love Belle.
Background[]
In the Enchanted Forest, the cup was chipped when Belle dropped it after she got unnerved from Rumplestiltskin's quip about skinning children, Belle keeping it despite the damage on the grounds that something shouldn't be thrown away just because it was broken, with the idea behind this statement inspiring much of Gold's later attempts to overcome his own darker nature to be with Belle. After Queen Regina claimed that Belle had committed suicide, he took the chipped cup and placed it on a pedestal.
In Storybrooke, Mr. Gold still treasures the cup. When Regina wanted to find out whether or not he remembered his past identity as Rumplestiltskin, she convinced Moe French to rob Gold's tea sets so she could get it. When Mr. Gold was arrested for torturing Moe, Regina arrived and bargained the cup for the information she wanted, and it was revealed that he too remembered his past life in the Enchanted Forest.
After the curse is broken, Belle walked into Mr. Gold's office and finds that he kept the chipped cup. She is very happy that Rumplestiltskin kept something to remember her by and she decides to stay with him.
After Belle loses her memories accidentally, Mr. Gold visits her in the hospital with the chipped cup. He gives it to her in hopes that she will recall her old memories. However, the subject of magic scares Belle, and she asks him to take the cup back but he insists she tries, but she refuses. In the midst of Belle trying to push the cup back, Belle takes the chipped cup and hurls it against the wall, where it shatters into pieces. Belle asks him to leave one, which he finally does in his despair of the destroyed cup.
Mr. Gold later manages to collect the shards of the cup and keeps them in the safe of his shop. When the Trigger to destroy Storybrooke is activated, he uses a potion given by Leroy that helps people regain their true memories, which must be drunk from an object that's important to them, and restores the cup from the shards. He then pours the potion in it for Belle and himself and has her drink it in a toast. Belle regains her memories and is reunited with Mr. Gold.
Henry is kidnapped and taken to Neverland by Greg and Tamara, leading Mr. Gold to join in on the journey there to rescue him in honor of Neal. While he believes the only way to save Henry from the villainous Peter Pan is to sacrifice his own life, Regina suggests that there must be a way to contain their nemesis. Mr. Gold has just the item for the job, except the weapon itself, is sitting in his pawnshop in Storybrooke, so Regina barters with a mermaid, Ariel, to retrieve it. Ariel is sent off to Storybrooke with a request from Mr. Gold to give Belle a magically enchanted sand dollar. Once the item reaches Belle's hands, she activates it to project an image of Mr. Gold along with a specific message from him. He informs her that she can indeed find the necessary item to defeat Pan "with the strength of their love". The riddle puzzles Belle until she thinks of the one item that is symbolic of the wear and tears their love has been through, which is the chipped cup. Unsure what to do with the cup, she places it back in the cupboard on a saucer; triggering a spell to open a hidden compartment on the floor. Inside, Belle finds Pandora's Box.
While Merida takes a break, the chipped cup is sitting in front of Gold, who's tied up. He reaches for the cup and kisses it before whispering "I'm sorry Belle" and smashes the cup so that he can use one of the pieces to break his ropes. It's last seen in shards when Merida and Emma find that he escaped.
In the Edge of Realms, after Mr. Gold and Belle build themselves a new home there, they decorate the inside of the house, with the chipped cup being one of the items placed on display. Following Belle's death, Mr. Gold has the chipped cup placed on her coffin.
Somehow, the chipped cup ends up in Hyperion Heights while the curse is in effect. When Tilly starts to regain memories of her old life, she leads Weaver to an alley shed and shows him the cup in an attempt to jolt him into remembering his true love. Weaver is confused and instead points out that it's just a chipped cup. Growing frantic that he is not waking up as he should be, Tilly makes a grab for Weaver's gun and points it at him. Weaver questions why she is doing this, to which she angrily reveals he told her to. Tilly then shoots him, and upon seeing Weaver collapse in a pool of his own blood, she is so shocked by her own actions that she drops the cup, shattering it into pieces. Weaver later attempts to fix the chipped cup.
