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I am trying to block some servers on computers based on keywords that would be contained in Url.

I know how to do it partially by using Internet Options -> Security.

However I am limited to using wildcards in a very specific way, for example, I can do *://*.xxx.com, but not allowed *://*xxx* which is what I am looking for.

Also, blocking websites would only be a part of a job, as I also need to restrict connections to specific servers being made by programs. (I might need to split question here if you believe this is too broad, please let me know. Although I think a solution that blocks it a 'connection being made' level, on Network card I presume, would block any connection I think.)

How do I block URLs based on a specific words or a pattern?

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You need a firewall that supports rules with wildcards, which unfortunately is not available in the Windows firewall.

A free product that supports asterisks in rules is Comodo Firewall.

Some more information about Comodo Firewall:

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