I've never "lost" a fight in the way that I was worse off than my opponent, I generally walk away without much need of medical assistance outside painkillers a bandaid and bedrest... That said, though I have trained in a variety of combat styles, I'm no master, and when I fight, I fight dirty, and I tend to use what I know to inflict the most harm to a person within reason that I can, I aim for balls solar plexus eyes and throat, if someone wants to kill me, it's adviseable to use a firearm from a distance, as I fight with the tenacity, ferocity, and rage of a cornered rabid grizzly, I am semi-suicidal, I don't care about death, I have little to live for, and as an exploratory person I'm kinda intrigued to see how it feels, and what it's like, to die...
I am not however going to kill myself pre-maturely, as there is too much to explore and see and experience while alive, and will fight, and struggle to the end...
Against 5 guys I estimate, that until one of them got behind me, I may be able to cripple or severely wound 2-3 of them before I had to bail or was overcome... if I had a baseball bat or a table leg or something, then it may turn out differently, as I tend to hit really hard with blunt implements, I broke apart a wooden shed at someone's request in a couple hours using nothing but an old dented aluminum baseball bat, which by the end of it, didn't really look like a baseball bat anymore, was kinda bent.
However, I tend to avoid such situations with my ability to talk people down, and make allies easily, every time I've lived in a bad neighbourhood, I've acted as something of a community diplomat, and have been on the good side of most if not all of the more dangerous people in the area, I don't choose sides, and tend not to associate directly with groups/gangs or authorities, but when it comes down to it, I also am not disposed to share information on anyone with anyone else, and as such, lemme just say, one day, I gave relationship advice to a Biker who recently got out of jail, and was trying to patch stuff up with his girl, met up with a bro of mine who was a dealer at the time, and smoked a joint with him and shot the shit for a couple hours, and ended up wandering onto the nearby reserve and having a beer with some of my native homies, in the 4 years that I lived in that area, known for crime and violence, I never had to fight, nobody wanted to hurt me, and I was poor as dirt, so nobody ever saw me as a mark to rob or mug.
I prefer diplomacy over violence, but my hands/feet/elbows/knees/forhead are all perfectly comfortable dispensing blunt trauma when need be, I just, prefer harmony and brotherhood over violence and dissorder...
Also being how the legal system in Canada is, I'd prefer not to fight if I can avoid it, as self defence in some cases will land you in jail for the same time penalty as the guy who attacked you in the first place, especially if you're armed with anything other than your hands, or have any high level martial arts training.
Also, advice for would be brawlers, never get a black belt in any martial art unless you want to be immediately in the wrong in the eyes of a courtroom if you get in a legal battle over a violent confrontation, and dont carry a knife(unless you're well trained with it, otherwise you may end up being stabbed with it yourself) or gun(unless allowed through a concealled carry permit where available) obvious reasons.
That or just prepare yourself for the worst, but walk a path of peace, and diplomacy, and you'll probably be fine, or at least have backup to fight alongside you, should shit hit the fan.