Let me start off by saying i love both these gloves. They are in my top 3 for gloves. That being said they each have their flaws but the good part is they arent major flaws. I recommend both whenever i can. Leather, Construction, Quality The leather of both these gloves works. Its not some cheap, easy to tear, ugly leather. That being said Winnings leather is better, its softer, smoother, and more vibrant. The Winning leather is without a doubt a higher quality, its my favorite leather even beating out Reyes. I only found one blemish on the otherwise perfect leather where it seems like some of it got ripped off but its a very very small scratch. Ring To Cages leather is more of a flat color, its not shiny but i still like it. My black 12ozs have a slightly messed up area where it seems a bubble almost formed in the leather, no big deal though just a blemish. They also have very small spots, like 1-4 almost microscopic size spots where the leather like flaked off or something. Besides those blemishes the leather is otherwise perfect. My red 16oz on the other hand, the leather is perfect and it looks slightly more vibrant because of the lighter color but still nothing compared to my black or blue Winning leather. When it comes to leather Winning definitely wins but R2C isnt far behind, R2C's leather is practical and efficient, Winnings just looks a little better and feels better. Construction on both gloves is excellent. Winning has perfect stitching, i only saw two loose threads but the stitching is otherwise perfection. Its straight, elegant, its eye catching in my opinion but for the right reasons. Same goes for R2C, their stitching is great, its straight, its elegant, theres no loose stitching. Construction on both these gloves is pretty good. The only bad thing about the C17s would be the ends of the piping, they look all tattered and worn out since day one, the ends are all messed up. WInnings piping looks great and well kept, they stretch the ends out of the piping and it just makes the gloves that much more attractive. Both gloves are overall great quality. Winning wins in this regard though. The materials used, the craftsmanship, the attention to detail, its all just on a whole different level. In my opinion Winning reigns supreme when it comes to these aspects. Looks/Hand Compartment They're very similar gloves, the C17s were obviously inspired by them. They look almost identical, same sort of thumb, beautiful double cuff for lace ups. Stitching is almost in identical spots. One thing that the C17s absolutely beat the Winnings im though is the velcro versions. Velcro on the C17s look great and its also more practical. Thicker and also with piping which i love. Winnings velcro works and works better than most but its very thin and flimsy. It makes the glove look awkward, i dont see the point of such a thin weak looking velcro strap. The velcro C17s also have an elastic on the palm side that connects the piping. I dont really see the point in having this but i know some people like it, Winning doesnt include it. Both gloves also have no vent holes whatsoever. The C17s are also more flat which isnt a bad thing but they feel bigger. The hand compartment is bigger, all around bigger specifically wider. Keep in mind im comparing 14oz winnings vs 16oz C17s but the hand compartment size is very very noticeable at least for me. For example without a wrapped hand i can shift my hand around the 16oz gloves, side to side. With the Winnings though i cant, i have very limited space. I also need to use less knuckle padding for the Winnings because if i use the same amount as i do for the C17s then the glove becomes a little uncomfortable around the knuckles, theres no pain but theres that feeling of tightness and i like things more loose. The finger compartment is better on Winnings for me, i can really wrap all fingers around the grip bar. For almost all my 16oz gloves though i can never wrap my pinky around them, thats including the C17s, again this is probably the oz difference playing a part but still the difference is noticeable enough to mention. The 12oz hand compartment of the C17s is more comparable to the hand compartment of the MS-500s. All that being said i have very small hands, im 5'5, ive never measured my hands but they're definitely small. I have had other people try on my Winnings and even with their bigger hands they still found the gloves to be very comfortable. When it comes to hand compartment though, if you have big hands id go with sizes 16oz+ on both the Winnings and C17s while keeping in mind that the C17's hand compartment seems to be a little bigger especially wider than the Winnings. Thumb/Padding Both the thumb and padding are my favorite of any other glove. I consider these two aspects of both gloves to be perfection. The thumb on each glove is straight. It helps to align everything into a perfect fist. Its extremely comfortable and thats coming from someone who hasnt had any thumb issues with any gloves. Part of the reason i got the C17s in a higher weight though was because my hands got sore and cramped up when using the Tokushus. I personally dont consider this a big deal, my hands were nice and sore the next day, like an extra little exercise. The C17s and MS-500 have never cramped up my hands. The kind of fist you can make in these is just ideal. The comfort of these gloves relies on that perfect thumb. That being said i have found the C17 thumb to be shorter than the Winnings, on both the 12oz and 16oz. The padding also ends before the leather does, that leaves a slight pinch on the tip if your thumb. For example on my 12oz my thumbs nail would be pinched, no pain at all but it loses some of that comfort. Then on my 16oz i have enough space for my thumb but if i move my thumb to the end of the gloves thumb then i can feel that the padding ends before the leather. Im not sure if its supposed to be like this or if its some type of QC issue, either way its not some glove breaking disaster, its just slightly annoying. Winnings thumb is longer than both these gloves, its also not as wide. Again demonstrating how Winning has the slimmer, sleeker design. Winning wins when it comes to thumbs. Theirs is just ideal and i have absolutely nothing to complain about. The padding on both is incredible. Above all this padding is the best for sparring. It protects your hand and it protects your sparring partner. You cant ask for more, the padding is excellent and ideal for sparring. That being said though both gloves can be used for anything. Bag work and mitts are both incredible with either glove. I have found that the padding of the Winning is more protective than the C17s. On a scale id say my 12oz C17s are the softest gloves, Ms-500s are slightly more firm, and C17s 16oz are the most firm. Take the word, '"firm," lightly though. These gloves are all extremely soft but comparing them to each other they each feel different. Considering that the C17s 16oz are more firm id consider them to be more protective for my hands than the 14oz Winnings but as i found out they arent. I managed to punch through the padding even with double the knuckle padding i used. I felt every knuckle that connected on the bag after i threw a left hook. Now let me say it didnt hurt, and i didnt hurt my hand or anything. I kept going after that for more rounds. It was more surprising than anything, i didnt expect that to happen ever. The MS-500s though, i havent been able to punch through them at all. I can hit the hardest part of my heavy bag and barely feel a thing. Theres no fear in hurting my hands when i use these gloves, they protect them so well its unreal. And again the surprising part is how i use less Le Roy wraps on my knuckles for my Winnings than i do for my C17s. Just a further example as to how protective these gloves are. To sum this up Winning wins on both the thumb and padding but thats not to say the C17s are terrible in these categories. The C17s are incredible and i take nothing away from them. I have yet to cramp my hands up when wearing them or injure my hands in any way. The MS-500s just have a slightly longer thumb which adds to the comfort and their padding is more protective to the point where you end up needing less wraps. Wrist/Liner The wrist on the lace ups of both gloves is my favorite. I love the double cuff, it has a great look to it. A single cuff looks fine, a triple cuff looks sort of obnoxious and weak, a double cuff looks excellent. The wrist support on both gloves is ideal especially for Winning. With Winning i havent hurt my left wrist when throwing hooks. The gloves do a great job to really align the wrist and keep it that way and take into consideration that i keep my gloves a little loose AND i use elastic laces. On my C17s 16oz though i have been able to hurt my wrists. Yes they're velcros vs laces but again is velcro vs loose elastic laces. Even so i havent hurt my wrists when using the Winnings but i do when i use the C17s to the point where i bought the Zrotwist wrist pad to add some extra support. This all being said though C17s velcro closure is tons better than Winnings in both performance and looks. When comparing my gloves though my Lace up Winnings wrist support beats both the 12oz and 16oz C17s. The liner is probably the most similar thing these gloves share. Both have an extremely soft liner, the Winning Ms-500s liner looks like blue waves while the C17s is just a solid black pillow. These are my favorite liners. For example in between rounds i rub the tip of my fingers on the top of the finger compartment to feel the liner. Its just so comfortable and it cools off pretty quick. The liner is yet another thing thats just absolutely ideal.