I have horse racing scheduled as a season pass, but it doesn't show up in scheduled recordings or on later. I was able to find it in the guide. It's listed as Horse racing, not sure why it didn't automatically get added.
Can you show a screenshot of your pass?
That may be the case.
It has been reported by several users over time in these forums that you can't trust the "New" tag. The guide data is not always accurate and may be missing the tag at times.
If you really want to record only episodes that have not aired yet (i.e. new episodes of the current season and beyond), it's more reliable to add an advanced rule with this condition:
SeasonNumber > 2
This example will record all episodes of season 3+.
Also make sure to record all episodes in this case (you should not have the condition "Tags == New").
Keep in mind that the DVR doesn't record duplicate episodes.
Your screenshot shows that there is 1 match.
Could you show the Advanced tab and the Matches tab?