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Being ready to fight unorthodox opponents is to me a fundamental part of self defense and something I've put a lot of thought into. Me, being unorthodox in the minds of most people I spar gives me an advantage for sure that people find very frustrating to deal with.
Being able to fight unorthodox opponents with no foreknowledge of the person is even harder because you have to be able to deal with what they show you as soon as they show it. You don't have a chance to watch tapes or try to find a similar sparring partner. So how do you go about doing that?
This is how I've done it:
For starting, you have to travel outside of your main training school to spar people. If you don't have a lot of traffic on an open sparring night that you can participate in, you have to go to other schools. There is just no way one building with one or two coaches can prepare you for the world because they will always be limited. You have to see it for yourself. I don't recommend this for people who are really new, but after a year or two and you have started to learn to move your body automatically and have gained some success sparring the people you know, it is time to find new people.
Secondly, you have to get to the source material. I like to start this early with people by showing them videos of street fights if they haven't seen them and getting them to spar early so that their own real nature is not suppressed by the drills. Then, when they become more advanced, it is important for them to spar hard with new people - but not to hit the new people hard - to protect themselves without causing too much pain or injury in the beginner. You want the beginner to have fun trying to HIT you, and to not be too afraid of repercussions, because those are the conditions of a real attack. It takes discipline and skill to be able to fend someone like that off without hurting them, and it isn't right to hurt new people when you know you can just go hard and break them, but you need to feel what they can do and see their surprises. Yes, it is dangerous for you, and if it feels too dangerous, you can always ask them to calm down.
It is always easier to stop someone from hurting you by applying damaging force than it is to protect and defend against someone not afraid of being injured. If you find you can't do it, suppress your ego and admit it.
Along the lines of source material, you need to look into why people attack the way they do, not just the natural tendencies of people but the logic taught by the different traditional and sport martial arts. I know it sounds arrogant to say you are training to beat a certain martial art, to identify weaknesses in groups, and to learn to look for those signs in people, but there is no other way of being prepared in a general sense for what they do. I'm not suggesting that you learn every martial art, but you should learn a little about how they train, what they like to do, and how to identify them by their stance, gestures, and appearance.
You know who can be surprisingly dangerous? Ninjitsu people. The specific group I know can't kick or punch for shit even though they think they can. They don't spar. And they don't wrestle. But they do this odd kind of sticky hands / counter for counter training where they try to show pokes to the eye and throat grabs. I trained with these people just long enough to get my arms scratched up by their fingernails and get poked in the eye, but I learned to identify their stance, what makes them different than karateka, even when they think they don't have a tell. I know when I see someone like that in sparring in the future, or in an assassination I guess, not to let them put their hands on me - to just punch them in the face because they can't stop it. To not bother with a clinch.
Some moves are typical and easy to put on other people without a set up. Some moves you can just lead with. They are better with a set up, but they don't need one - especially against people who don't know of them, and that makes them popular. Jab, cross, hook, single and double leg, MT round house, clinch and knee, reaping throw...
Then their are counters lots of people like: kicking under the punch, overhand rights during your combo, slipping and countering, stopping your rush with a double leg and so on. While a lot of that is normal combat sport stuff, if you just do most TMAs you might not know about them and that fact will contribute to you being shocked and bullied in sparring by even beginners despite how long you have trained. So you have to learn about them and to do that, a lot of us have to travel.
A lot of the strikers that people think are unorothdox look ordinary to me, great, but ordinary. Anderson Silva, Cung Le, Condit, I'm never surprised by what I see them do. Impressed yes, and happy, but not surprised. It is drawn on by things I think are ordinary. There are people I train with who don't counter much or use TMA style snapping kicks or counter striking, but they travel to and aren't surprised by me or anyone else when they see it. The first time I sparred them I did much better than the 20th, and when other TMA people came in they were ready for it.
At this point in my life, people almost never surprise me. I'm never surprised by the wildness of new people or "street fighters" that come into spar. It is just human movement. When people beat me, its because they are better than me, not because I was ignorant of their strategy. That cuts down on how often I get had by a lot.
Do it all enough, and you learn to read people. The intention to hit or grab or kick or come in fast or slow or straight or round or high or low is written all over people, even when they think they don't have a tell or a style, and the more time you spend with people and the more you let them learn about you, the more you learn about them. Truth is shared and you all become wiser.
