If you want to sort the items by considering the numerical values first(there are edge cases to consider, but should point you to the right direction):
from itertools import takewhile, dropwhile
test = ['3 Silver', '3 Oct', '4AD', '99 Reese', '1991', 'alpha', 'beta']
items = dict()
for word in test:
ordlist = []
## prenumber will be zero if there are no numerical characters
prenumber = int(''.join(list(takewhile(lambda i: i.isdigit() , word))) or 0)
## setting words that start with alpha characters to have infinity as
## first item. This puts them at the end of the list for sorting.
ordlist.append(prenumber or float("inf"))
ordlist.extend((ord(ch) for ch in dropwhile(lambda i: i.isdigit(), word)))
items[word] = ordlist
### sort dictionary by value
s = sorted(zip(items.values(), items.keys()))
print(s)
## [([3, 32, 79, 99, 116], '3 Oct'),
## ([3, 32, 83, 105, 108, 118, 101, 114], '3 Silver'),
## ([4, 65, 68], '4AD'),
## ([99, 32, 82, 101, 101, 115, 101], '99 Reese'),
## ([1991], '1991'),
## ([inf, 97, 108, 112, 104, 97], 'alpha'),
## ([inf, 98, 101, 116, 97], 'beta')]
test_sorted = [e[1] for e in s]
## ['3 Oct', '3 Silver', '4AD', '99 Reese', '1991', 'alpha', 'beta']