The most common and most likely answer to this crossword clue is the 5 plus 6 letter word FIRST FOOTER
I've seen this crossword clue in The Daily Telegraph
F
I
R
S
T
F
O
O
T
E
R
Buddy explains!
The straight part
We know that "Delivery man who may darken your doorway tonight" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case delivery man who may darken your doorway tonight = first footer.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.