|Season Two:||Chocolate Milk|
|Season Three:||New Captain|
Ray Holt and Madeline Wuntch are arch-nemeses although Wuntch seems to have unrequited affections for one Holt, despite his sexuality. The two are shown to mock and taunt each other on every available occasion.
- Wuntch is introduced as Holt's arch nemesis.
- Wuntch fails Holt's precinct.
- Holt blames Wuntch for his promotion failing.
- It is revealed, in a flashback that Holt and Wuntch used to be friends.
- Wuntch tried to seduce Holt before he came out as gay and he believes that's why she sabotaged his promotiom.
- It is revealed that Wuntch didn't sabotage Holt's promotion, she is angry for other reasons.
- Holt goes and apologises to Wuntch and she passes the precinct.
- Wuntch refuses Holt's request to help with "Giggle Pig" due to incorrect punctuation.
- Holt goes behind Wuntch's back and gets a task force.
- Wuntch tells Holt that she made him oversell "Giggle Pig" deliberately.
- Wuntch hires an internal affairs investigator to spy on Holt and his task force.
- Holt finds out and tapes her admitting her.
- Holt tells her to leave his precinct alone.
- Wuntch gives Holt a commendation for his work combatting "Giggle Pig"
- She is surprised when he doesn't gloat to her.
- Holt then changes his mind and shouts "Wuntch time is over" at her.
- Wuntch asks Holt to recommend Wuntch for a promotion.
- Holt decides to giver her a good recommendation.
- Wuntch tells Holt that she negotiated a more local promotion so she won't be moving.
- Wuntch says that she knows he wouldn't have recommended her if he thought she didn't deserve it and kisses him, leaving him confused.
- Holt thinks that Wuntch wants to take over his case but instead she says she will give him anything he wants.
- Holt realises that Wuntch wanted him to succeed and she says it has given her an excuse to promote him to a boring desk job.
- Holt finds a letter that Wuntch wrote being rude about the chief which he can use to overturn his promotion.
- Wuntch asks Holt how she knows he's not wearing a wire and slowly pats him down.
- Wuntch threatens to relocate Holt's squad if he won't comply and Holt agrees to take the promotion.
- Wuntch refuses to let Holt improve the PR department.
- The two fight over whether the mascot should be a pigeon and Wuntch forces Holt to name it.
- Wuntch forces Holt to wear the pigeon costume.
- Wuntch assigns Bob to watch over Holt which humiliates him.
- Wuntch is very angry when she finds that Holt has been secretly working the case.