import re
 
def extract_values(sentence):
   num = r'\d*\.?\d+(?:/\d*\.?\d+)*'
   matches = re.findall(fr'(({num})(?:\s+(?:and|to)\s+({num}))*)', sentence)
 
   result = []
   for x,y,z in matches:
       if '/' in x:
           result.append(x)
       else:
           result.extend(filter(lambda x: x!="", [y,z]))
   return result
 
# ['1 and 1/2', '.5', '5', '9 to 11', '9 to 9 and 1/2', '11/12/20']
print(extract_values("He is 1 and 1/2 years old. He is .5 years old and he is 5 years old. He is between 9 to 11 or 9 to 9 and 1/2. He was born 11/12/20"))
 
text = "Score 1 and 2 sometimes, often 1 and 1/2, or 2.5 or 3 and 1/3."
print( extract_values(text) )
 
# <1>, <2>, <1 and 1/2>, <2.5>, <3 and 1/3>

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