This is an attempt of putting Rumpelstiltskin's history into a chronological order, given events are shown out of order in canon. SPOILERS are unmarked and below. This also lists events that happened in regards to The Dark Curse.
Beginnings.
»» Rumpelstiltskin was recruited in the First Ogre War. He ran away from the war and was labeled a coward. (1.08 Desperate Souls)
»» After returning home, Rumpelstiltskin's wife couldn't stand being with a coward. She left him and died some point there after. He raised their son, Baelfire, on his own as the town's spinner. (1.08 Desperate Souls)
»» The war raged on and the Duke began to recruit children. Rumpelstiltskin and Baelfire attempt to run away, but are stopped by the guards. Humiliated by the guards, an old beggar tells Rumpelstiltskin the story of The Dark One who is commanded by the Duke. He convinces him to steal the dagger and command the Dark One. (1.08 Desperate Souls)
»» After retrieving the dagger, Rumpelstiltskin is egged on by the Dark One into killing him for his power to protect Baelfire. The Dark One, Zozo was actually the beggar. Now with the Curse of the Dark One, Rumpelstiltskin kills the guards coming after Baelfire and begins to fall into corruption. (1.08 Desperate Souls)
»» Rumpelstiltskin ends the Ogre Wars and makes both sides broker deals, saving the children and the lands. He gains respect, but quickly is feared as he torments and hurts those who lay a hand on his son. (1.19 The Return)
»» Baelfire convinces his father to make a deal with him. If Baelfire can find a way to end his curse, then Rumpelstiltskin will give up magic and be with his son as a normal man. Baelfire then asks Reul Ghorm - The Blue Fairy - for help. She gives him a magic bean that will take him and his father from Fairy Tale Land to a world with no magic. (1.19 The Return)
»» As the portal opened, Rumpelstiltskin couldn't give up his magic. He stuck the dagger with his name on it into the ground and held on. Baelfire was ripped away from him, calling his father a coward. Rumpelstiltskin then vowed to find a way back to his son, blaming the Blue Fairy for his son being ripped away from him. After learning from her that a curse would take him to the world Baelfire was in, Rumpelstiltskin began to work on the Dark Curse. (1.19 The Return)
The Dark One.
»» Rumpelstiltskin begins making deals to gain magical items and power. This is most likely to start creating and constructing the Dark Curse. This is over the course of centuries.
»» Jiminy is a man who wants to change his life, but must be free of his parents. Rumpelstiltskin offers him a deal. He gave Jiminy a potion and said that he would collect his parents after they had it. While Geppetto's parents are the ones who are turned to puppets, and Jiminy becomes a cricket to aid Geppetto through life, Rumpelstiltskin still collects his dues of parents turned into puppets. (1.05 That Still Small Voice)
»» Rumpelstiltskin visits a desperate woman named Cora. For an unsaid price, he gives her a book that would teach her magic. Cora's future child - Regina - would somehow tie into this. (2.02 We Are Both)
»» King George and his Queen are unable to conceive a child and go to Rumpelstiltskin for aid. For an unknown sum of money, Rumpelstiltskin goes to a farm that is struggling. He offers to take one of the twins to make sure the family farm succeeds, but they must never speak of the deal. The son that was taken becomes Prince James. (1.06 The Shepard)
»» Soon-to-be-Queen Regina summons Rumpelstiltskin in hopes of finding a way to be free of her mother. He gives her a Looking Glass that would send Cora to another world for no prince. He then urged Regina along in pushing her mother through the Looking Glass. (2.02 We Are Both)
»» Queen Regina attempts to ride to safety to be confronted by Rumpelstiltskin. She tries to give him the book of spells back, but he hands it back to her in the hopes of teaching her magic. In return, she will do something for her one day - possibly use the Dark Curse (2.02 We Are Both)
»» Sir Maurice seeks a way to protect his people from another Ogre War. Rumpelstiltskin makes the deal that for protection, he must give up his daughter: Belle. He is looking for a caretaker for his estate. Belle agrees to the terms and comes to live at Rumpelstiltskin's caste. (1.12 Skin Deep)
»» Queen Regina manipulates the Genie into killing King Leopold and she truly becomes The Evil Queen. (1.11 Fruit of the Poisonous Tree)
»» **Rumpelstiltskin trades the Dark Curse to Queen Regina. (1.02 Things We Love Most)
»» Rumpelstiltskin begins to fall in love with Belle, and she him. He allows her to leave the palace to go to the market. He doesn't believe she will return. (1.12 Skin Deep)
»» Belle meets Queen Regina on her way back from the market and learns how "true love's kiss" can break any spell. When she returns and kisses Rumpelstiltskin, the curse begins to break. Convinced she is now working with Queen Regina, Rumpelstiltskin locks her away then banishes her from his presence. (1.12 Skin Deep)
»» Queen Regina comes to Rumpelstiltskin about a deal to get rid of "a little mermaid." She then lies to him and tells him that Sir Maurice had locked Belle away and ordered an "exorcism" that caused Belle to jump from the tower. Rumpelstiltskin mourns Belle, but Queen Regina holds her captive. (1.12 Skin Deep)
»» King George summons Rumpelstiltskin to bring Prince James back from the dead. Rumpelstiltskin agrees to fix his problem and in return wants the whereabouts of the Fairy Godmother. Rumpelstiltskin retrieves the twin brother for King George. (1.06 The Shepard)
»» **Queen Regina trades the Dark Curse for Maleficent's Sleeping Curse to poison the apple for Snow White. (1.02 Things You Love Most)
»» Snow White seeks out Rumpelstiltskin for a way to forget her heartache. For a potion to remove the memories of her love, Rumpelstiltskin takes strands of her hair. (1.10 7:15 AM)
»» Grumpy takes Snow White to Rumpelstiltskin in hopes of reversing the potion. Instead, Rumpelstiltskin gives her a map and a bow that "never misses it's target." His payment is that he is "invested in her future." (1.16 Heart of Darkness)
»» Prince "Charming" James seeks out Rumpelstiltskin for a way to find Snow White. In return for his cloak, Rumpelstiltskin gives him the location of Snow White. (1.16 Heart of Darkness)
»» Rumpelstiltskin takes a hair from Charming's cloak along with Snow White's hair and creates the True Love potion. He then uses one drop of this on the parchment of the Dark Curse to ensure that their child would break it. (1.16 Heart of Darkness, 1.22 A Land Without Magic)
»» Rumpelstiltskin enchants Prince Charming's mother's ring in order to find Snow White. The price is putting the True Love potion inside the belly of Maleficent as a dragon. (1.22 A Land Without Magic)
»» Prince Charming finds Snow White and wakes her from her sleeping curse with love's true kiss. He proposes to her and they vow to take the kingdom back. (1.22 A Land Without Magic, 1.01 Pilot)
»» **Prince Charming and Snow White take back the kingdom.
»» At the eve of Prince Thomas' ball, Rumpelstiltskin kills the Fairy Godmother and takes her wand. Creating a contract with Cinderella, he then sends her off with glass slippers to the ball. (1.04 The Price of Gold)
»» **Wedding of Snow White and Prince Charming. Queen Regina threatens to destroy their happiness. (1.01 Pilot)
»» **Prince Thomas and Cinderella are married. Rumpelstiltskin makes himself known and informs Cinderella that he wants her first born as a price of her new life. (1.04 The Price of Gold)
»» **Snow White becomes pregnant with her child. (1.01 Pilot)
»» Cinderella tricks Rumpelstiltskin with a second deal early in her pregnancy. Prince Thomas disappears as a price of capturing Rumpelstiltskin, who is then imprisoned in a cell carved out by dwarves. It holds magical properties to seal him there. (1.04 The Price of Gold)
»» Snow White seeks out Rumpelstiltskin's help for Queen Regina's warning. In return for telling her about the Dark Curse, Rumpelstiltskin learns that the unborn child's name is Emma. (1.01 Pilot)
»» Queen Regina retrieves her Dark Curse and tries to enact it. With it being failed, she goes to Rumpelstiltskin in hopes of learning why. For telling her that she had to cut out the heart of what she loved most, Rumpelstiltskin would receive power, comfort and that she must listen to whatever his command is when he uses the word "please" in the new land. (1.02 The Thing You Love Most)
»» Rumpelstiltskin is consumed by the curse and becomes Mr. Gold, complete with memories of his Fairy Tale Land life as he created the curse. (1.01 Pilot)
NOTE: ** marked events are ones that do not have a cemented place in the timeline. This namely effects "The Price of Gold" in relation to the events of the Snow White storyline.
It is unknown if Snow and Charming are married at Cinderella's wedding, but they are happily seen in public together. The end events of "The Price of Gold" must happen before Snow White is pregnant due to Rumpelstiltskin's imprisonment.
When the events of "Skin Deep" happen is unknown, besides the fact it must be after King Leopold's death because Regina dresses in black and is queen. It is possible the deal was made before King Leopold died but ends after Regina has been queen and Snow White is in hiding. However, "Dreamy" happens after Belle is banished but before Regina captures her.