The matchmaking always worked the same. It doesn’t care about ribbons, it only cares about rank. So if you are in Silver you get (mostly) set up with other silver players. (There is also a reason they are in Silver and not in the higher divisions.)
And 500 wins is not that much and doesn’t tell you anything about their skill either. It only tells you they played more but oh man did I see players with a lot of ribbons make beginner mistakes…
I would recommend to look at what you can improve about your gameplay. If they are better players than you then you could try to learn something from them by rewatching the replay and thinking about your and their positioning. Positioning is the most important skill in that game.
Here you can find guides about positioning, disenchanting, deckbuilding and budget decks which offer enough power to reach s-rank with them (with certain amount of skill). It also tells you how to get free orbs.
https://duelyst.gamepedia.com/New_Player_Guides
If you want more practical advice tailored to your playstyle, send me a friend’s invite (same name) and I can do a replay analysis for you. I would happily help you out.
You will find out at some point that not the ribbons are the decisive factor. Duelyst is a difficult game to learn and there are a lot of small mistakes you can do without even realizing. Learning the basics and having a solid deck will give you most of the edge you need to keep up with the more experienced players. The rest comes with play time 



