The most common and most likely answer to this crossword clue is the 7 plus 9 letter word PENALTY SHOOT-OUT
I've seen this crossword clue in The Guardian
P
E
N
A
L
T
Y
S
H
O
O
T
-
O
U
T
More clues leading to the result PENALTY SHOOT-OUT
Buddy explains!
The straight part
We know that "when England generally loses?/when England generally loses?" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case when england generally loses?/when england generally loses? = penalty shoot-out.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.