According to re docs
^ (Caret.) Matches the start of the string, and in MULTILINE mode also matches immediately after each newline.
$ Matches the end of the string or just before the newline at the end of the string, and in MULTILINE mode also matches before a newline. foo matches both ‘foo’ and ‘foobar’, while the regular expression foo$ matches only ‘foo’. More interestingly, searching for foo.$ in 'foo1\nfoo2\n' matches ‘foo2’ normally, but ‘foo1’ in MULTILINE mode; searching for a single $ in 'foo\n' will find two (empty) matches: one just before the newline, and one at the end of the string.
This is not case in your example. You would need to use more advanced zero-length assertions.
(?<!\S)\d+\/\d{2}(?!/)regex101.com/r/DwnXit/1^and$. They mark the start and end of a line or string, in combination your regex only matches a full line.