Sorry, no online dictionaries contain the exact phrase least winning.
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Reverse dictionary results:
1. euchre
 2. break
3. draw
4. knockout
5. even
6. prizewinning
7. primary
8. ace
9. distance
10. hair
 11. inch
12. qualify
13. ray
14. rope
15. roping
16. tear
17. bottom
18. bottoms
19. cheap
20. down
 21. passive
22. set
23. slowest
24. smaller
25. sure
26. taste
27. under
28. worse
29. worst
30. pentathlon
 31. evens
32. gamesmanship
33. hearts
34. mira
35. miracle
36. nick
37. odds-on
38. slam
39. slamming
40. take

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You can look up the words in the phrase individually using these links:   least ?   winning ?
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Not helpful? You might try using the wildcards * and ? to find the word you're looking for. For example, use
leas*to search for words beginning with leas, or
*ningto search for words ending with ning
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