re.search() finds the pattern once in the string, documenation:

Scan through string looking for a location where the regular expression pattern produces a match, and return a corresponding MatchObject instance. Return None if no position in the string matches the pattern; note that this is different from finding a zero-length match at some point in the string.

In order to match every occurrence, you need re.findall(), documentation:

Return all non-overlapping matches of pattern in string, as a list of strings. The string is scanned left-to-right, and matches are returned in the order found. If one or more groups are present in the pattern, return a list of groups; this will be a list of tuples if the pattern has more than one group. Empty matches are included in the result unless they touch the beginning of another match.

Example:

>>> import re
>>> regex = re.compile(r'([a-z]+)', re.I)
>>> # using search we only get the first item.
>>> regex.search("123hello456world789").groups()
('hello',)
>>> # using findall we get every item.
>>> regex.findall("123hello456world789")
['hello', 'world']

UPDATE:

Due to your duplicate question (as discussed at this link) I have added my other answer here as well:

>>> import re
>>> regex = re.compile(r'([a-z][a-z-\']+[a-z])')
>>> regex.findall("HELLO W-O-R-L-D") # this has uppercase
[]  # there are no results here, because the string is uppercase
>>> regex.findall("HELLO W-O-R-L-D".lower()) # lets lowercase
['hello', 'w-o-r-l-d'] # now we have results
>>> regex.findall("123hello456world789")
['hello', 'world']

As you can see, the reason why you were failing on the first sample you provided is because of the uppercase, you can simply add the re.IGNORECASE flag, though you mentioned that matches should be lowercase only.

import re
if re.match(regex, content):
  blah..

You could also use re.search depending on how you want it to match.

You can run this example:

"""
very nice interface to try regexes: https://regex101.com/
"""
# %%
"""Simple if statement with a regex"""
import re

regex = r"\s*Proof.\s*"
contents = ['Proof.\n', '\nProof.\n']
for content in contents:
    assert re.match(regex, content), f'Failed on {content=} with {regex=}'
    if re.match(regex, content):
        print(content)