Real wing tsun sparring is a rarity in WT schools.
The main reason is that their sifus tell them they don't need sparring because chi sau and lat sau training is enough for learning how to fight. Unfortunately, that is nonsense. All that leads to is student exclusively practicing in the middle distance where most of chi sau and lat sau happens. They don't spend enough time practicing the all-important first part: the initial attack and all the fakes and draws usually employed by fighters from other systems and styles.
Sure, we have the Lat Sau programs in wing tsun, but those rarely evolve into real free sparring. Yes, wing tsun fighters are supposed to train to close the gap immediately so you rarely see any of that typical thing where two guys circle each other and dance around, feinting, moving, looking for an opening or trying to create one and then coming in for the kill.
If you don’t practice with people who do that (and who are good at it, i.e., not with your own students if your are a teacher or with fellow wing tsun students), you will never know where your pitfalls are.
Yes, wing tsun is “theoretically perfect” - but what good is that to you if you don't know your own weaknesses? If you're a sifu, your students surely can’t show them to you. If you are a student, your sihings and sidais are more likely than not mentally locked into the same routines that you practice, simply because both you and they are practicing them all the time.
If you’re not actually used to various people dancing around you in the old sparring routine and then launching real attacks on you without holding back, you get nailed. End of story. Here is a classic example of that:
This is where you likely are in your WT training. Don’t make the same mistakes.
This guy does it better:
What are the first WT (wannabe) fighter's mistakes, then?
(A) He simply stands there in his wing tsun pose, waiting for his opponent to attack. He forgot the first principle in wing tsun: If the way is free, attack!
(B) When he kicks, he is out of range (using his front leg from a distance; the rear leg has far longer range), and when he misses he doesn't follow through and continue the attack. After all, the way to his opponent is still free.
(C) He hasn’t sparred enough, so he doesn’t recognize the super-committed attack for what it is. His opponent figured out that he stops and regroups after a missed kick, so the opponent lets him kick and then plows right through him with his hyper-committed "haymaker" punch. The wing tsun fighter is a sitting duck. Rather than letting the attacker’s power go by or preempting it with his own follow-through attack, he "blocks" it - with his face.
I am not knocking the WT fighter’s skill here. This video was taken after he had trained only one year. He is now a respected sifu. It’s just a fact that he made mistakes, and the mistakes he made are very typical for wing tsun fighters - even advanced ones.
So, what’s an aspiring wing tsun fighter to do?
Find out where your weakness lies against a “live” opponent (i.e., against someone who really is trying to hit you as hard as he can and who doesn’t fear you because you are his “sihing” or his “sifu” or whatever). In essence, do what Morten did here.
Isolate that area of weakness and work on it. Most likely, it will be the initial “bridging the gap” moment. NEVER stop after a halfhearted attack. KEEP MOVING IN and follow through, so your opponent stays on the defensive.
If the principles and tactics you learned in class lead you away from the wing tsun mottoes, and if your own wing tsun sifu can’t give you better pointers that enable you to incorporate the mottoes, stop practicing wing tsun. It’s not for you.
If following the principles (mottoes) more closely does help you perform better, do the same thing against a variety of other opponents.
Rinse and repeat.
To do this, it's best to make friends with a number of people from other MA systems and schools. Don’t let your sifu tell you that you shouldn’t do that. If he does, look for a new sifu, maybe. He should not limit your development like that. He should encourage you to do this. After all, when you signed up for class, you didn't sign up to become a cult member. You signed up to learn a martial art that is based on common sense and human physiology - and one that works under all circumstances..
If the common sense you learn in wing tsun class doesn’t work in the real world, it probably isn’t common sense. Then it’s probably what I call 'wing tsun dogma' - and dogma and wing tsun are fundamentally incompatible. If you find dogma in your school, change your school - fast! You are not learning wing tsun there. You are being inculcated with a martial arts religion. Run!