The most common and most likely answer to this crossword clue is the 9 letter word INFIELDER
I
N
F
I
E
L
D
E
R
Buddy explains!

The straight part
We know that "silly point possibly" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case silly point possibly = infielder.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.
What does INFIELDER mean?
INFIELDER noun- A player who plays in the infield, which is the inner portion of the field.