Expecting win, they may fail abysmally (2,3,6,3)
I believe the answer is:
in the family way
'expecting' is the definition.
(I've seen this before)
'win they may fail abysmally' is the wordplay.
'abysmally' indicates anagramming the letters.
'win'+'they'+'may'+'fail'='wintheymayfail'
'wintheymayfail' is an anagram of 'IN THE FAMILY WAY'.
(Other definitions for in the family way that I've seen before include "Expecting" , "carrying child" , "pregnant" .)