Two or more people wish to either court/woo or outright marry another, but perhaps the target of their affections isn't sure who to choose, or perhaps the suitors discover their rivalry and decide to compete to see who will drop out of the running (whether with or without the knowledge or approval of the maiden). 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. Related to Engagement Challenge and can be a Secret Test of Character, or not so secret test of character. Can lead to Murder the Hypotenuse or a Cock Fight if one of the suitors doesn't accept the contest or doesn't like the outcome.
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- 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 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.
- In Romeo and Juliet, Romeo and Paris are both competing for Juliet's hand—but neither of them know it. Paris thinks he's got the goods because of his title (a Prince no less) but the moment Juliet makes eye contact with Romeo at her father's ball, she's pretty much made up her 13 year old mind. And Paris never finds out. When Romeo ends up killing Paris outside Juliet's family's mausoleum, only then does Romeo acknowledge any sort of rivalry.
- 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.
- 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.
- Arcanum's backstory 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.
- Those romancing Josephine in Dragon Age: Inquisition will discover that she has been betrothed to a Lord Otrano. The Inquisitor can arrange to duel Otrano behind Josephine's back, but Josephine shows up to stop the duel. If the Inquisitor affirms their love for Josephine, Otrano will approve of their love and withdraw his engagement.
- At one point in Baldurs Gate 2, 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.
- 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' 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.