Regex to match URL end-of-line or "/" character

/(.+)/(\d{4}-\d{2}-\d{2})-(\d+)(/.*)?$

1st Capturing Group (.+)

.+ matches any character (except for line terminators)

• + Quantifier — Matches between one and unlimited times, as many times as possible, giving back as needed (greedy)

2nd Capturing Group (\d{4}-\d{2}-\d{2})

\d{4} matches a digit (equal to [0-9])

• {4} Quantifier — Matches exactly 4 times

- matches the character - literally (case sensitive)

\d{2} matches a digit (equal to [0-9])

• {2} Quantifier — Matches exactly 2 times

- matches the character - literally (case sensitive)

\d{2} matches a digit (equal to [0-9])

• {2} Quantifier — Matches exactly 2 times

- matches the character - literally (case sensitive)

3rd Capturing Group (\d+)

\d+ matches a digit (equal to [0-9])

• + Quantifier — Matches between one and unlimited times, as many times as possible, giving back as needed (greedy)

4th Capturing Group (.*)?

? Quantifier — Matches between zero and one times, as many times as possible, giving back as needed (greedy)

.* matches any character (except for line terminators)

• * Quantifier — Matches between zero and unlimited times, as many times as possible, giving back as needed (greedy)

$ asserts position at the end of the string

To match either / or end of content, use (/|\z)

This only applies if you are not using multi-line matching (i.e. you're matching a single URL, not a newline-delimited list of URLs).

To put that with an updated version of what you had:

/(\S+?)/(\d{4}-\d{2}-\d{2})-(\d+)(/|\z)

Note that I've changed the start to be a non-greedy match for non-whitespace ( \S+? ) rather than matching anything and everything ( .* )

You've got a couple regexes now which will do what you want, so that's adequately covered.

What hasn't been mentioned is why your attempt won't work: Inside a character class, $ (as well as ^, ., and /) has no special meaning, so [/$] matches either a literal / or a literal $ rather than terminating the regex (/) or matching end-of-line ($).