I need to read this so much. When I spar at kickboxing, I can NEVER get close to this guy, the top guy in the class, nationally ranked and all. He is like 4 inches taller than me and has realllly long legs, everytime I try to get in on him he just stuffs me with a side kick and it fucks me up. He is so fast and powerful with his legs, he gets like 5 kicks on me before I can blink. However, when he trades with me, I always get the best of it and end up either knocking him down or putting him off balance. I always ahve to take some punishment to get in and even if I can get in and fuck him up, he'd always win the point game.
Sorry man, this post got overlooked but it just so happens I have an exercise that may help you be able to get in on this guy's kicks. See in my class one year we had this TKD dude come out who stood about 6'2"-6'3". A lot of my Gung Fu students could never, ever get close to him because not only did his legs never fucking end, but he did TKD, primarily a kicking Art. Before they could even get anywhere remotely near punching range Brandon would have already lit them up with a front-snap-side-kick into a step-in side-kick combo. Only my Muay Thai student could get in on him because D.J. knew how to attack the legs. And he even got his lip bloodied for his troubles.
So I noticed (because paying a lot of attention is what made me a decent fighter/trainer) that we needed to develope an exercise that taught split-second timing to move from kicking to punching range. Now I don't think we "invented" this, but I never did see it before. This exercise is not only good to train up timing, reflexes, accuracy, and speed, but it's also fun as HELL and a GREAT way to take out frustrations in your class. Most times when doing this both of my students participating would end up chuckling and trading insults. I encouraged being aggressive and mean. lol
Trading Kicks with the Blocking Pads:
Now if you're schooled in kicking Arts and how to use certain kicks properly you know that nothing disrupts a kick like a counter-kick that's faster and simpler. I always encourage if you have an opponent who likes to throw fancy-pants kick techniques, RIGHT when he STARTS to move, throw a front-kick or teep as fast and hard as you can. This works beautifully especially if he's going for a spinning-kick or head-high kick. You'll knock him over more times than not, or at the very least a couple of steps back. This guy you're talking about counters with a side-kick, pretty fancy and smart, kind of made me smile picturing your utter confusion at getting stuffed by it. lol But you can stuff him in-return. Bye the way, don't let him see you practicing this or he'll get wise to it pretty quick.
So, to train up your speed, accuracy, sense of timing, and even power for countering a kick with a kick here's what you do. Have a partner who is maybe a little better than you, or at least equal skill hold a blocking pad and you hold one yourself. Pick a kick, and both of you fire the kicks at the same time. It's going to be very fast and messy at first. My students used to just try and machine-gun each other off their feet. That's the rule of the game. First one off their feet or to give-in loses. If you want to work with boundaries have a circle, maybe 10 feet in circumference either drawn or taped off, and first to the boundary loses. What you're going to notice when you do this is which of your kicks are weak, strong, fast, slow, etc. After like the first few minutes you'll both start getting tired and this is where the real fun begins. Because now it becomes a chess game. I rememeber periods of like 30 seconds where two of my students would just be there smiling at each other, sucking wind, then out of NOWHERE one would pop a spinning-back-kick. The other would attempt to stuff it with a teep. Sometimes it worked out, other times they got knocked on their ass.
When two students got really good at it they hardly threw any kicks, but the ones they did made a HUGE impact. They had graduated beyond just trying to overwhelm each other with kick combinations and into marksmanship with their kicks. So fast and accurate it was extremely difficult to catch one or counter. When two students were of equal skill it was like watching a car accident. Both would fire a kick at the EXACT same time and nature had to determine who came out the better. lol
It's a fun exercise and works on a lot of things at once. Speed, power, accuracy, timing, as I already named, plus it gives you an idea of your conditioning and how to conserve your energy if you're going to use kicks.
If you want to do this and train leg-kicks and head-high kicks at the same time that's easy enough, dawn head-gear and shin guards if you have them. But the head-high kicks cannot be full-power unfortunately. Do this for a couple of months and that dude is going to find it harder to stuff you because you'll stuff him right back with say a front-kick. Now, if you pair this with one of the other exercises in my initial post, over time you'll even be able to side-step and deliver a kick of your own. Making him miss entirely and eat one of your kicks. But that's a ways away and he'll hopefully be tough to do that to.
Hope this helps.