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There are 23 clues with the answer 'COULDA'
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CLUE
1.
Might've, informally
2.
Had the opportunity to, casually
3.
"Woulda, ___, shoulda"
4.
Middle of a regretful trio
5.
Part of a wistful trio
6.
Might've
7.
Bit of hindsight slang
8.
new debut album by #18-Across: '___ Woulda Shoulda'
9.
Might have, informally
10.
Part of an "if only ..." lament
11.
"I __ been a contender"
12.
"I ___ been a contender"
13.
"I ___ been a contender!"
14.
Woulda-shoulda connector
15.
Woulda, ___, shoulda
16.
May've
17.
Colloquially, might firm use lender's leads I supplied (6)
18.
Woulda partner
19.
Just might have, slangily
20.
'I ___ been a contender'
21.
'I ___ been a contender!'
22.
"___ Been the
23.
'I __ been a contender'