She was born and raised in the state of Kentucky.
It is unclear when Winona met her future husband, Raylan Givens. They met in Salt Lake, and were married for six years. They promised themselves they would never return to KY.
It was after Raylan's posting in Glynco, Georgia that their marriage began to deteriorate. Raylan's anger-management problems, and the fear of being the widow of a dead US Marshal, drove Winona to divorce Raylan and marry their realtor, Gary Hawkins.
Winona moved back to Kentucky after her mother fell ill. She worked as a court stenographer at the Lexington Federal Courthouse, which would cause her to be reunited with Raylan.
Winona soon leaves Lexington in order for her and Raylan's unborn child to have a better life and not be endangered by the dangers of Raylan's career, and begins to live with her sister Gayle until the baby is born. Winona also resigns from her job as court sternographer at the Lexington Federal Courthouse, and is replaced by Mabel Johnston.
Winona and Raylan renew their relationship by making love.
Winona and Raylan renew their relationship and start dating.
She spontaneously steals an old $100 bill from the evidence locker in the US Marshal's Office. Later in the season, it is revealed that she stole all of the money from the locker. She convinces Raylan to help her return the money without alerting the authorities. As she returns the money to the evidence locker, Art Mullen, Raylan's boss, catches them but does not say anything.
In "The Gunfighter" Winona learns of Raylan's shooting and rushes to the hospital to be with him. She is pregnant with his child. She helps to care for him as he recovers from his gunshot wound over the coming weeks, and even moving into his motel room. She and Raylan are held at gunpoint in the room by Fletcher Nix but Raylan is able to wound and capture Nix.
In "Cut Ties" Winona puts the house she shared with Gary on the market. Raylan accompanies her to an ultrasound scan as part of her prenatal care. When she learns that one of his colleagues has been murdered she comes to his office to show her support. In "Harlan Roulette" Winona and Raylan discuss viewing a property together, but Winona has to go alone when Raylan is called to work.
In "Thick as Mud", Winona is now seven weeks pregnant with their unborn child. Raylan comes home late to find her waiting for him. She reminisces about the first night she was reunited with Raylan when he scared Gary in her kitchen. Raylan senses that she is angry. Winona says that she is done trying to change Raylan, and that she's done pretending she could feel the way about any other man that she feels about Raylan. Raylan says that it may be the sweetest thing he's ever heard from her, and the two kiss. Raylan returns home at the end of the episode to find his house empty and a note presumably left by Winona, which appears to be bad news due to Raylan's reaction after reading it.
In "When the Guns Come Out", Raylan finally manages to get a lead on Winona's location from Tom Bergen, who tells him that while Raylan was in the hospital, Art put out a BOLO on Winona, who was located outside of Louisville. Raylan locates her at her sister Gayle's house, and they begin to talk. Raylan suspects her of stealing the money from the evidence locker to go to Costa Rica, and she tells him that she didn't steal it. Winona tells him that she didn't want the baby to be raised in an environment where Raylan shoots and kills people. She then tells Raylan that if he wanted to change his life around, he would have done so by now.
In "Watching the Detectives", Winona is brought back to Lexington after learning about the death of Gary, since she is a suspect from Gary Dempsey's view of exes automatically being suspects in murder cases. Winona is distraught after Raylan tells her the bad news. Winona also learns that Gary was involved in the hit on her and Raylan, and is angry with Raylan for not telling her earlier and leaves. Later, she finds a gun planted at her house and Raylan asks her to bring the gun to him at a park. She asks if Raylan is going to throw the gun off a bridge, and tells Raylan not to come and find her this time as she drives off.
In "Slaughterhouse", Raylan visits her to check on her and tells her about the whole ordeal that had went on in "Coalition" and previously in Slaughterhouse. Raylan has a drink of water and Winona tells him she plans to stay at Gayle's until the baby is born. Raylan promptly excuses himself because of the time, but Winona asks him why Art would think he was upset over Bergen's death. Raylan theorizes that it was because of the reason Arlo shot Bergen: Arlo had not known Bergen was a State Trooper, he just saw a man in a hat with a gun pointed at Boyd. Soon after Raylan leaves, Winona figures out that Arlo had assumed he shot Raylan and not a State Trooper.
In "Kin", Winona meets Raylan before one of her doctor's appointments. He tells her that he is in charge of one of the biggest cases that the Marshal's office has seen, but she doesn't seem too impressed. Raylan leaves before the appointment when he has to deal with work.
In "Peace of Mind", Winona calls Raylan to ask if he had signed paperwork for their unborn child, and Winona then confirms that they are having a baby girl. Later, Picker (the henchman of Nick Augustine) disguises as a delivery man and puts together her rocking chair.
In "Ghosts", Winona is held hostage by Cobb, Lex, and Dominic to be used as leverage so that Raylan will be forced to get them to Drew Thompson. Raylan manages to dispose of the captors and a protection team is sent to watch over Winona. Raylan vows to her that he is going to find the person responsible.
- Raylan Givens: Ex-husband and father of her unborn daughter
- Gary Hawkins: Ex-husband (since season 2), deceased.
- Gayle: Sister
- Arlo Givens: Former father-in-law, deceased.
- Frances Givens: Former mother-in-law, deceased
- Mike Reardon: Judge
- Art Mullen: Chief Deputy US Marshal
- David Vasquez: Prosecutor
- Mabel Johnston: Successor as court sternographer
"Raylan, you do a good job of hiding it. And I s'pose most folks don't see it, but honestly, you're the angriest man I have ever known."
|Season one appearances|
|Fire in the Hole||Riverbrook||Fixer||Long in the Tooth||The Lord of War and Thunder|
|The Collection||Blind Spot||Blowback||Hatless||The Hammer|
|Veterans||Fathers and Sons||Bulletville|
|Season two appearances|
|The Moonshine War||The Life Inside||The I of the Storm||For Blood or Money||Cottonmouth|
|Blaze of Glory||Save My Love||The Spoil||Brother's Keeper||Debts and Accounts|
|Full Commitment||Reckoning||Bloody Harlan|
|Season three appearances|
|The Gunfighter||Cut Ties||Harlan Roulette||The Devil You Know||Thick as Mud|
|When the Guns Come Out||The Man Behind The Curtain||Watching the Detectives||Loose Ends||Guy Walks Into a Bar|
|Season four appearances|
|Hole in the Wall||Where's Waldo?||Truth and Consequences||This Bird Has Flown||Kin|
|Foot Chase||Money Trap||Outlaw||The Hatchet Tour||Get Drew|
|Decoy||Peace of Mind||Ghosts|