Was OT prophecy really fulfilled?

Matthew 8:14-17

Matthew continues to pile on evidence that Jesus is not just an ordinary rabbi but is the Messiah. He doesn't just teach with authourity, as evidenced in the Sermon on the Mount, but he also acts with authourity over the physical realm, as seen by his healing of diseases, and the spiritual realm, as seen by his casting out demons. I don't know if Matthew meant to emphasize the method of healing or not but it stands out to me: he heals the centurion's servant without even being physically present, he heals Peter's mother-in-law in such close proximity that he touches her and he casts out demons through the power of his word. I think that Matthew is reminding us that it is not a formula that has the power to heal but it is Jesus.
Matthew connects what Jesus does here to Isaiah 53:4, following his usual formula of "this was to fulfill what was written..." He uses this phrase a lot. Keeping in mind that Matthew was writing to a Jewish audience to convince them that Jesus was the Messiah, this constant reference to the prophecies of the OT makes sense. However, as a Gentile living thousands of years later, I'm not sure that they would convince me. It seems like Matthew reads a lot into the text of the OT to make parallels between what it says and what Jesus does. In talking to Pastor Steve about this, he said something that made a lot of sense to me: Matthew and his audience would have been so familiar with the OT that they couldn't help but make comparisons between what Jesus did and what the OT said. The reality is that much of what Matthew says was fulfilled in Jesus was actually fulfilled soon after the prophecies were made (not 100% but a lot). In Bible College I was taught that this was because there were two fufillments of these prophecies: the more immediate fulfillment and then the actual, later fulfillment in Christ. This could be true but it raises the question: are the only prophecies to have double fulfillment the ones that are specifically mentioned in the NT? What is to prevent us from seeing double fulfillment in other OT prophecies?
Pastor Steve wonders if we don't understand how Matthew was using the world "fulfill". We take it to mean that Isaiah had Jesus and/or the Messiah in mind when he spoke these words. Maybe Matthew and his audience understood it as "this is just like what Isaiah talked about...". I need to do more study on that.
So, what do I learn from this? I am reminded that Jesus is King - not just of my heart and not just of the Church but of the whole world. He has authourity over all things physical and spiritual. What do I need to be afraid of? Nothing!