This trope only applies if one suitor challenges at least one other suitor to the contest. If the contest is imposed by a third party, such as by the maiden's father or by the maiden herself, then the example belongs in Engagement Challenge.
Despite the name, this trope applies equally to both males competing for the affections of a female and females competing for the affections of a male. It also applies to same-sex relationships. The trope name was chosen only because it's the most well known version of the trope.
Very much Truth in Television for the animal kingdom and has sometimes happened with people.
- The trailers for the (as of early April 2017) about-to-be-released 21th Case Closed movie, Crimson love letters, state that a gender flipped version of the trope will take place. Both of Heiji's potential girlfriends, Kazuha and Momiji, are proficient in a card game called hyakunin issha garuta, and will compete against one another and many other students in a karuta tournament. This coincides with Momiji being Heiji's Self-Proclaimed Love Interest, confronting both Heiji and Kazuha on their potential love triangle, and Kazuha deciding to challenge Momiji both in love and karuta....
- Adapted for high school participants in an episode of Yu-Gi-Oh! GX: A 3rd year Jerk Jock (tennis captain) who falls in Love at First Sight with Alexis becomes jealous when he sees she treats Jaden much friendlier than she does him, so he challenges Jaden to a duel for the right to become her "fiancé." Jaden accepts because he never turns down a chance to duel (for her part, Alexis just finds the whole thing absurd). Jaden wins... and immediately asks what a fiancé is.
- In ElfQuest, Rayek challenges Cutter to The Trial of Head, Hand and Heart with the winner of all three trials having the unchallenged right to "woo" Leetah.
- In Superman's Pal: Jimmy Olsen (2019), an unnamed galactic warlord who believes Jimmy "stole" his bride, the space princess turned Classy Cat-Burglar Jix, by marrying her first, challenges Jimmy to a fight to the death for her. Jimmy replies that he has no intention of fighting to the death for anything, and it's entirely Jix's decision anyway. (She doesn't want to be married to either of them, and Jimmy has already started divorce proceedings. But they're Amicable Exes.)
- Wonder Woman Vol 1: Kenyah imposes a challenge for Nubia expecting to fight other men for ownership of her more than anything resembling marriage, instead she furiously answers him with:
"I claim the right to name my champion, Kenyah! One who will meet you on equal ground to battle for possession of me! I [name] myself!"
- Dangerverse: When Luna catches Amanda Smythe flirting with Draco (whom she has been quasi-engaged to for several years), she proposes that they undertake essentially a challenge of flirting. Each of them will take turns flirting with Draco while the other stands back over alternating two-month periods, and whichever of them Draco likes better is the winner.
- Gender-Inverted in the Codename: Kids Next Door fanfic Weddings, Teams, and Fortune tellers where Lizzie and Numbuh 362 are competing for Numbuh 1's affections, with the added catch of him not actually knowing about it.
- This is ostensibly what it comes down to in the final jousting match in A Knight's Tale, though for the villain, and to at least some extent the hero, it's really about pride.
- An Invoked Trope in The Life and Death of Colonel Blimp. A British officer and a German officer fight a duel over political issues, but as this could cause problems with their superiors they pretend they're doing it for the honor of a woman they both know.
- Extreme Prejudice. Texas Ranger Jack Benteen and former friend-turned drug kingpin Cash Bailey duel for Sarita, even though her own response to this is You're Insane!. Really though these two have been heading for a gunfight one way or another, so they may as well do it for the woman they love.
- In High School U.S.A., J.J. and Beau have a drag race to compete for the right to date Beth.
- Dead of Night: In "The Golfer's Story", Parratt and Potter are in the love with the same woman, who cannot choose between them, so they play a round of golf for her hand, with the winner earning the right to marry her.
- Kaamelott: At the start of its Cerebus Syndrome, Arthur starts courting Mevanwi, the wife of one of his knights, Karadoc of Vannes (Guenièvre having already run off with Lancelot by that point). When the latter is finally made aware of it, both reluctantly prepare to fight to the death for her (Karadoc wasn't that interested in her in the first place, while Arthur doesn't want to have to kill one of his own knights). Fortunately, he finds an old Vannes law where two people can exchange wives, averting the duel. Unfortunately, it turns out Mevanwi is a Manipulative Bitch and Guenievre isn't exactly living the dream either, so the exchange is later cancelled.
- In The Movie, Kaamelott: Premier Volet, knight wannabe Kolaig wants the hand of Guenièvre (whom he wants to free from Lancelot) as he thinks it's part of his quest to become a knight. He also thinks he has to kill Arthur to do so, despite Arthur not giving a damn anymore about Guenièvre (at least at first). He's prevented from killing Arthur and gets explained what's really up now that Arthur is back.
- In Declare, Philby and Hale play a poker game for Elena. Their first game on Mount Ararat is interrupted, but their second one in Moscow leaves Hale the winner. Philby wins the immortality elixir, but it doesn't bring him happiness the way being with Elena brought it to Hale.
- Jay Gatsby and Tom Buchanan in The Great Gatsby both vie for Daisy's love. The twist here is that Tom is already married to Daisy and Jay is attempting to steal Daisy away from him. The reason Jay thinks he's entitled is because they met and fell in love before Daisy met Tom. In the end, the decision rests on poor ol' Daisy.
- In The Knight's Tale from The Canterbury Tales, Arcite and Palamon meet in Theseus' garden, intending to fight a duel to decide which of them will have the right to court Emily. When Theseus interrupts the duel and learns why they are fighting, he decides to organise a tournament with Emily's hand in marriage as the prize.
- Time Wars series: After Andre joins the Corps, Lucas and Finn agree on a drinking contest to settle which of them gets to make a move on her. She learns about it and insists on being allowed to join the contest, wins it handily, and claims as her prize a night on the town at their expense without either of them.
- Mentioned by Dave Barry on the subject of elks mating: the two male will bash their heads in until the female wanders off, depressed at the idea of having to be with one of these two idiots, while the victorious and nearly brain-dead male will then attempt to mate with anything including nearby shrubbery.
- This happened in the backstory of Cullyn of Cerrmor in the Deverry novels. The only thing that kept him from being hung over killing his opponent was the fact that witnesses stated that the other guy started the fight. He did end up exiled from his home city and forced to become a mercenary, with the woman in question choosing to follow him and ending up a barmaid in the only tavern in a nothing village in the middle of nowhere. Cullyn would later swear an oath to never again kill over a woman - it doesn't do any good for any of the involved parties, a decision that allows him to break free of a four-hundred year old chain of wyrd.
- In the backstory for A Song of Ice and Fire, Catelyn Tully was betrothed to Brandon Stark, who was challenged by Catelyn's foster brother Petyr "Littlefinger" Baelish for her hand. The two dueled and Brandon gave Petyr severe injuries, including a cut from navel to collarbone. It turned out neither man would get her when Brandon and his father were executed by King Aerys "The Mad King" Targaryen and Catelyn married Brandon's brother Ned.
- Used as part of a Batman Gambit in The Legend of Sun Knight. Royal Knight Elijah loves the princess of his country, and while she returns his affections, she's bound to a political marriage with the head of the War God's religion. To help Elijah, Sun also proposes to the princess, and suggests that all three of them duel. However, the point of the duel wasn't to make Elijah win, but for him to be in a position to publicly perform a Diving Save when the princess is attacked by a monster note . Such an act of devotion cannot be denied by the gods, so both Sun Knight and the head recant their proposals.
- In Confession Executive Committee, this is the premise of the Idol Series in-universe music video for "Romeo". The Princes of the West and East are both separately trying to woo an unhappy princess, but once the men learn of the other's existence immediately decide to duel each other to have the honor of properly courting her. The princess, enamored with both men, is heartbroken that they'd ever resort to this and cries. They are on much better terms by the time the sequel video "Julieta" comes out.
- In Trials & Trebuchets, Phillip challenges Prince Frederick to a duel for Serinepth's hand as a last-ditch effort to prevent her Arranged Marriage to the prince from going through. Serinepth is able to call this duel off by confessing to the prince that she has no intention of marrying him as she does not love him, though this does have the unfortunate side effect of the prince declaring both her and Phillip's families traitors to the crown as punishment for this Breach of Promise of Marriage.
- Our Miss Brooks: In "The Grudge Match", Walter Denton challenges Stretch Snodgrass to a fight for Harriet Conklin's love. The two end up boxing in a temporary ring setup in the Madison High School gymnasium.
- The backstory in Arcanum: Of Steamworks & Magick Obscura has a duel between Garrick Stout and Adkin Chambers over who had the right to court Lady Druella. Stout won, but dishonorably gouged out Chamber's eyes after the latter had admitted defeat, causing Druella to hate him and refuse his advances.
- AdventureQuest Worlds has the King's Tournament for the 2013 Heroes' Heart Day event. The winner of the tournament becomes Swordhaven's War General and wins the right to court Princess Brittany, the oldest of the Princesses of Swordhaven. Your character fights in the place of Lord Brentan, probably the most suitable candidate for both major conditions, after he is treacherously struck down by Sir Roderick of Grimreaver, who seeks to win the Tournament at any cost in order to seize the throne of Swordhaven from King Alteon.
- Baldur's Gate 2:
- At one point, you can see two NPCs duel to the death of the affections of a lady, who, upon the duel's conclusion, points out that she wasn't really interested in either of them and walks away.
- There's also a gender-swapped version, with a guy seeing his girlfriend at the Copper Coronet back rooms while his wife is out looking for him in the main area. If you tell her where he is, she'll confront them, whereupon the girlfriend pulls a knife and they fight. If the girlfriend wins, she'll drag him off to be married properly, whereas if the wife wins, he'll be enamored with her for it and return home with her.
- If your character is in process of courting Aerie and you have Haer'Dalis on your party, he flirts on her and eventually challenges your character into a duel to compete for Aerie's hands. The duel won't actually happen, as the player character's reaction (either trying to avoid the duel altogether or jump at the chance) will force Aerie to make a decision, but the trope almost happened for real (which may result you having to kill Haer'Dalis, because the other outcome will be an instant Game Over). This will not happen if your romance has been solidified before Haer'Dalis would start flirting, wherein he takes his tardiness' consequences with grace.
- Those romancing Josephine in Dragon Age: Inquisition will discover that she has been betrothed to a Lord Otranto. The Inquisitor can arrange to duel Otranto behind Josephine's back, but Josephine shows up to stop the duel. If the Inquisitor affirms their love for Josephine, Otranto will approve of their love and withdraw his engagement.
- In Fable, the Romance Sidequest for Lady Grey, Mayor of Bowerstone, requires the Hero to duel a rival suitor for her hand: Thunder, a fellow Guild Hero, who's been hostile to the Hero throughout the game.
- This is the crux of the eleventh New Yankee in King Arthur's Court game, Battle for the Bride. Sir Lancaster, The Friend Nobody Likes of the heroes, has a beautiful daughter, Olwen, who is in love with the king's nephew Sir Culhwch; however, Lancaster is holding a competition to see which of her many suitors is most deserving of his beloved daughter. Arthur tasks John and Mary with helping Culhwch succeed at Lancaster's increasingly bizarre Engagement Challenges while outwitting his evil rival... and a goblin chieftain, and an irate genie, and...
- Sid Meier's Pirates!: Every town allows a Romance Sidequest with the Governor's daughter, each of whom has a Disposable FiancÚ who needs to be dueled at the midpoint. Defeat permanently ends the quest line for that daughter.
- All-Star Superman turns this into a three-way when Superman has to compete against the time-travelling duo of Atlas and Samson in a contest of feats for Lois's hand after she flirts with them. They eventually settle this with a double arm-wrestling contest.
- The Mickey Mouse cartoon Mickey's Rival Returns has his rival Mortimer Mouse challenge him to one-on-one beach volleyball for the right to date Minnie. Mickey wins, but Mortimer twists the events (with a handy Quote Mine) in Minnie's presence to make Mickey seem chauvinistic, and thus Mortimer actually winds up going out with Minnie. He blows his chance, natch.
- In the Daffy Duck short Muscle Tussle, Daffy's girlfriend is wooed by a beach strongman; Daffy tries to prove he is the other guy's better but fails.
- In Moomins on the Riviera Moomin duels Clark after he thinks he sees him trying to kiss Snorkmaiden.
- A Gentlemen's Duel is about two men dueling over who has the right to court a lady... with steam-powered Humongous Mecha. However, neither party bothered to ask what the lady's opinion of the matter was before initiating the duel.