The most common and most likely answer to this crossword clue is the 8 letter word LOVESOME
I've seen this crossword clue in The Daily Telegraph
L
O
V
E
S
O
M
E
Buddy explains!
The straight part
We know that "Winning" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case winning = lovesome.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 LOVESOME mean?
LOVESOME adjective- Worthy of love; having qualities that inspire love; lovable.
- Lovable on account of beauty; lovely; beautiful; winsome.
- Marked or characterised by love; loving; manifesting love or affection; affectionate; friendly.
- Amorous; romantic.