The rules of masculinity say that a man cannot be beaten by a woman. Of course, any such man who is beaten by a woman is pretty unhappy.
Rationale for No Guy Wants an Amazon. Waif-Fu may be in evidence. Related to Samus Is a Girl, if the man wasn't aware his opponent was female before losing. May be the punishment of the Straw Misogynist, whose sole purpose is to be beaten by the woman.
Often the only thing more humiliating to a believer in machismo is to be defeated by a cripple.
Unfortunately Truth in Television. Ironically prevalent among men who know little about fighting; any man involved in martial arts for very long knows just how lethal a woman can be.
Not to be confused with Double Standard: Abuse, Female on Male, but may be the reason some victims of that trope are afraid to come forward.
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Anime and Manga
In Codename: Sailor V Takurō Ōtaku refuses to believe his high scores have been trounced by a girl, even accusing Minako of being a man in disguise.
Averted in Dragon Ball Z when Vegeta is thoroughly defeated by Android 18, he was more concerned with the fact that he could be beaten at all despite finally becoming a Super Saiyan. He was actually angrier that it was a "machine" that did it than a girl.
Interestingly, Piccolo at least thinks Vegeta has this attitude, if he doesn't have it himself.
(Not exact quote) Piccolo: "He was soundly beaten, by a female at that! I can't imagine what that could have done to his pride."
The latest chapter of Little House with an Orange Roof has Rina bragging that she beat all the boys in her class at arm wrestling. Youta is shown looking humiliated with a note indicating he was one of the losers.
One episode of Lucky Star happens in an arcade, where Konata beats several people in succession. When her opponents try to see who it is that beat them and realize it's a very young-looking girl, they quickly leave.
Samurai High School: One of the guys Tsukiko defeated had this reaction upon learning it was her and not her brother who defeated him.
Averted in Attack on Titan. Eren is soundly trounced by Annie during combat training, and is immediately impressed with her skill. This leads to them becoming close friends, with her teaching him how to fight.
In the Superboy story introducing the Legion of Super-Heroes, Superboy's first task in order to join the team is to compete against Saturn Girl (part of the main Power Trio of the Legion) in retrieving a sunken statue from the ocean. However, Superboy is just barely on his way when he gets sidetracked by a crisis involving the local school's robot Superboy. By the time he resolves it, Saturn Girl has completed the task. When both returned to the clubhouse, Cosmic Boy takes the opportunity to rub it in:
Cosmic Boy: You lost out on your first task... and to a girl! Is this the great Superboy we learned about in school? What's your excuse?
Happens to Ken Mills of Dork Tower, as his girlfriend Sujata regularly trounces him at whatever games they play.
Comes up a few times in Birds of Prey, most notably when Dinah trounces a group of religious extremist terrorists. Because dying honorably in battle is believed to be a guaranteed ticket into Heaven, the man Black Canary has at her mercy refuses to talk— until she questions whether being killed by a woman counts.
Midway through the Azula Trilogy, Azula has a run-in with a psychotic waterbending pirate. He comes back as The Dragon in the third part, itching for revenge after being beaten by a teenage girl. Fittingly, he just gets his ass kicked by Katara this time.
In Takamachi Nanoha Of 2814, Superman loses a fight to Vita due to his weakness to magic. Everybody makes fun of him, even Batman.
Films — Animated
In The Lion King, Simba gets pinned by his girlfriend Nala on three separate occasions. Though in his case he eventually returns the favor.
Averted in Mulan. Though Shan-Yu is understandably furious with Mulan for destroying his army, he doesn't particularly seem to care that she is a woman. He's also one of the few male characters in the whole film who never outright says anything sexist towards Mulan, either.
In Monsters vs. Aliens, Doctor Cockroach mocks the Missing Link for being "out-monstered by a girl."
In Hoodwinked, the Wolf relates his side of the humiliating story of getting beaten up by Red Puckett.
Nicky Flippers: So! You really took a beating, from a little girl? [Cuts to Red standing next to a picture of herself as the "Forest Regional Karate Champion"]
Films — Live-Action
Uttered (in almost exactly same words, no less) by one of the heroes of Polish cult sci-fi film Sex Mission, after, well... It (like many other quotes from this film) has since entered Memetic Mutation.
Implied and subverted in Deep Red, the protagonist scoffs when his female counterpart claims that a woman can be just as strong as a man. She challenges him to an arm wrestling contest in which he begins to lose. He stops and claims she is cheating somehow and gives it another time before almost losing again and stopping to make similar complaints. It's obvious he did not want to invoke this trope.
Averted in "A Scandal in Bohemia": Sherlock Holmes, who Does Not Like Women, finds out that the adversary who managed to tail him home, then escape from him, is a woman named Irene Adler. He is greatly impressed and a little bit smitten.
In Half Magic, Katharine wishes to beat Sir Lancelot in a joust, and then has to unwish it when Lancelot is mocked by the other knights because he was beaten by a girl.
In The Bible, we have the story of Abimelech, who was mortally wounded when a woman dropped a millstone on his head. He had one of his men kill him so that people wouldn't say that a woman killed him.
In Silicon Wolfpack, Murgatroyd gets KO'd by an Action Girl because she thinks he's trying to steal her car. His friends naturally think this is hilarious, and one of them points out that speed and flexibility count for more than power.
When Margo and Malcolm spar in Time Scout, their first two bouts go to Malcolm. The last two go to Margo. That he, an experienced guide twice her age, got manhandled convinces him he hasn't been spending enough time at the gym. That she, too, is spending time there is just a bonus.
The reason why Elend refuses to spar with Vin. Though this has less to do with Elend being macho (he's not, particularly) and more to do with the fact that he's king and Vin is tiny. Knowing full well that she'd beat him, he'd rather not get curbstomped in front of his subjects by someone who's barely five feet... and his girlfriend.
Gerald Tarrand, Villain Protagonist of Coldfire Trilogy is not remotely pleased to learn that the Evil Sorcerer who defeated him in the first book is actually a woman using a masculine title. Of course, the fact that he's a vampire who normally prefers to feed on young women makes it a particularly galling role reversal for him.
On The Amazing Race 17, men from two different teams made a number of comments about how they felt of the possibility of losing to either of the female teams, Nat & Kat or Brook & Clair. Thomas, who finished third behind the two female teams in the finale, averted this, as he admitted that the female teams were the two best teams.
Harlem Globetrotters Flight Time & Big Easy begrudgingly acknowledged sisters Kisha & Jen's racing skills in the Season 18 finale, though their hyper-competitiveness meant they probably would have had this reaction to any team beating them.
Chip (Season 5) had this reaction after getting smoked by the Bowling Moms in what he described as "putting together a car," but was really just decorating it by attaching a bunch of pieces to it.
An episode of Buffy the Vampire Slayer had Xander react with annoyance when Buffy rescued him from a school bully, which is distinctly different and more ego-deflating than the times she saves him from demons.
At the end of the Doctor Who episode "Utopia", the Master utters his anger at having been fatally wounded by Chantho. His next self is killed in a similar fashion by Lucy in "Last of the Time Lords" and jokes that women often do that.
In Malcolm in the Middle, Reese gets his ass kicked by a female wrestler in a match, which demoralizes him and causes him to try and be nice, which in turn creates the bully power vacuum that later arises.
Prince Arthur from Merlinreally doesn't want to fight Morgause but can't back out without losing face. He ends up incredibly embarrassed anyway when she beats him. Arthur rationalizes the situation to himself by saying that he let her win because she's a woman; Merlin is unconvinced.
In an episode of Neds Declassified School Survival Guide, Mose beats Ned in gym during a martial arts class, causing the local bullies to give him grief that he was beaten up by a girl. Ned seeks the help of Gordy, who simply tells him fighting a girl is a no win situation, as if you lose, you just got beat by a girl, and if you win, you just beat up a girl. In the end, this is resolved by Ned and Mose flipping said bullies to show them how wrong they are.
The Sontaran Kaagh from series 2 of The Sarah Jane Adventures is humiliated at being beaten by "a female and half-forms". He survives his first appearance, but feels unable to return to Sontar out of shame, and ends up working for the main villain in the series finale.
Stargate SG-1: A tribal chieftain, Turghan, gets owned by Carter. And she had a much smaller knife, too.
Supernatural - The Winchesters are hunting a monster who assumes the form of its victim's idol. Its most recent victim was a teenage girl. The fight ends with Sam cutting its head off and a beat-up Dean on the ground.
John Crichton of Farscape, so very much. The first episode features him getting his ass handed to him by Aeryn; it doesn't really stop. Doubly amusing as John's a pretty buff guy, all things considered.
On All That a dummy of a character would often be used to indicate he or she was being tossed around. In an old west sketch Nasty Nancy (Kenan Thompson) and Dusty Pants (Josh Server) fought the Slappy Brothers (Kel Mitchell and Leon Frierson). Kenan hits them with a dummy of Christy Knowings. Leon remarked that he can't believe they were beat by a woman. Kel notes they weren't just beat by a woman, but beat "with" a woman.
On Cold Case, Scotty and Lily are transporting a prisoner wanted for the presumed murder of a woman who disappeared several months earlier. Scotty taunts him about the fact that it was HIS blood found at the scene rather than the victim's, meaning that she'd managed to put up a decent fight—"You get your ass handed to you by a woman, Johnny-boy?"
Omega Zell from Noob gets a few interactions with this trope. The tournament from the comic has him fight against Golgotha and he get geunine fear of loosing against her due to the fact that he has shown hints of not entirely considering her a woman (he considers all his other female peers as unable to overpower him). In the webseries, he lets his loss of a Curb-Stomp Battle with Saphir pass due to her being a much higher level player than he is, but doesn't take loosing his first real duel against Gaea well at all.
One song by Phil X and The Drills contains the choice lyric "I'm the air hockey champion of the world, of the world ... except for the time I got beat by a girl!"
In Norse Mythology, Thor once lost a wrestling match to an elderly woman, and everybody makes fun of him. Learning that she was Elli, the Anthropomorphic Personification of Old Age, who cannot be defeated because nothing is immune to aging, not even the Gods, doesn't cheer him up.
In Puccini's "Tosca" the female protagonists stabs the complete monster Scarpia in the gut; "that was Tosca's kiss". Realizing the wound is fatal his reaction is: "Oh killed by a woman, what a disgrace."
Miyako Matsumoto defeated Survival Tobita at Ice Ribbon New Aisuhiro #493 - Muscle Venus 5th Anniversary, August 25, 2013.
AIW Women's Champion "The AK-47" Allysin Kay defeated Kobald at AIW The End of the World, December 21, 2012.
Sara Del Rey pinned her ex-BDK stablemate Tim Donst to win the Torneo Cibernetico at CHIKARA Cibernetico: The Animated Series, November 12, 2011, making her the first and so far only woman to do so. Earlier in the match, she had eliminated the BDK's monster Tursas.
In Advance Wars, Eagle expresses his surprise when Sami, who has just beaten his whole army, turns out to be female.
Seedle from Makai Kingdom was a famous samurai in life, and died when a woman stabbed him while he was trying to rape her. He really hasn't gotten over it, especially since said woman was burned as a witch for killing him and ended up in the Netherworld alongside him, eventually becoming one of his rivals.
One of the pre-recorded taunts in Age of Empires II is "Oh, you just got beaten by a girl."
In BioWare's original Neverwinter Nights game series, one of the female player character's voice options says, in a stentorian fashion, "Prepare to be beaten by a girl!"
In Lollipop Chainsaw, when Juliet Starling defeats Vikke in a boss battle, Vikke has a Villainous Breakdown and screams, "Impossible! I can't be beaten by a little girl! I'm a warrior!"
In The Antithesis, the first episode of the story (I. The Encounter) recounts Alezair Czynri nearly getting killed by Leid Koseling in the battle of Jerusalem circa 1180. Alezair's ego is significantly damaged by this, and this initiates the entire story, making him want to pursue her and perhaps fight her again. Later in Decus, Qaira Eltruan gets his ass beat by Leid on numerous occasions after losing his temper (or after she makes him lose his temper), and often he becomes so impossible to deal with that she must smack some sense into him. This is also ego-damaging to Qaira, since he is what we would deem a "manly-man", also a chauvinist, and also a misogynist. Although the readers find Qaira's beat-downs rather funny, Qaira, in fact, does not.
In the Whateley Universe, huge Montana (who looks like a Sasquatch) gets challenged to a fight by petite Sassy Black Girl Chaka, who proceeds to utterly pwn him. In front of a big portion of the school. This does eventually lower his jerk quotient.
This happens in an episode of Avatar: The Last Airbender when the Kyoshi Warriors jump and tie up the trio, and it turns out they are all female. Sokka refuses to believe that a "bunch of girls" captured them, and tries to argue that "sneaking up" doesn't count as a fair fight. Confronting them later only confirms that they can in fact best him in a fair fight.
And then he ends up dating one of them.
Duncan from Total Drama Island was demolished by his own girlfriend, despite mentioning early that he wasn't going to let her win.
Inverted in Futurama, Zapp Brannigan is actually happy when he finds out that the guy who just beat him was actually Leela in disguise. Relieved because he was starting to have... feelings for "him".
Mr. Garrison: Stanley, can I talk to you for a minute?
Mr. Garrison: I couldn't help but notice that black eye you have. Are there problems at home?
Mr. Garrison: Oh dear. Here Stanley, sit down, have some cocoa, and tell your friend Mr. Hat all about it.
Mr. Hat: I'm your friend, Mr. Hat, Stan. You can tell me anything. Now, who hits you, is it your father, or your mother?
Stan: Oh, neither. It's my sister.
Mr. Garrison: Your sister?! Oh for Pete's sake, don't be such a little wuss. Stop wasting Mr. Hat's time with pansy little foo-foo problems, and, give me back my cocoa!
Imagine the shame of being a muscle-bound henchmen who just got your butt handed to you by a cheerleader, even Kim Possible.
She-Ra: Princess of Power Skeletor responds like this when She-Ra makes her first appearance, and knocks the stuffing out of him: "A female He-Man! This is the worst day of my life!"
This also happens in an episode of Adventures of the Gummi Bears in which Princess Calla defeats every man in a tournament before losing to a masked challenger... who turns out to be a girl as well.
While this could qualify for any villain beaten by The Powerpuff Girls, this explicitly comes up in "Members Only". The girls are not allowed to join the Association of World Super Men because they're girls despite besting the heroes at all the initiation tests. "Mascumax" then pummels the heroes, but the girls defeat him. He leaves crying that he lost to little girls. The association members state that the girls are now their heroes.