| CHANCE | Probability, the ... of winning |
| EVERT | Identify the surname of this legendary woman tennis player who holds the record of most consecutive 13 years of winning at least one major title (5) |
| ICEHOCKEY | Canada holds a record of winning this sport the most number of times with a total of 21 medals: 2 wds. |
| WEIGHTLIFTING | China holds a record of winning this sport the most number of times with a total of 266 medals: 2 wds. |
| ARI | Actress Graynor of Winning Time: The Rise of the Lakers Dynasty |
| SEDUCTION | Act of winning the love of someone |
| SLIM | Like the odds of winning the lottery |
| GRANDSLAM | Feat of winning all the tricks in a hand of bridge (5,4) |
| MONEYBALL | Michael Lewis best seller with the subtitle "The Art of Winning an Unfair Game" |
| WAR | Game with the objective of winning all the cards |
| BRINKMANSHIP | Negotiating tactic of making credible threats in the hope of winning concessions (12) |
| DEV | Captain of winning team of the '83 Cricket World Cup |
| RICH | Many people dream of winning the lottery, but if you're willing to work hard, there are lots of other ways to become ___ |
| SWAHN | Identify this family that holds the record of winning the most medals in Olympic history for a father and son duo? (5) |
| ODDS | Scraps the chances of winning (4) |
| ANOSE | The smallest of winning margins |
| UPON | At the time of winning Oscar, primarily nervous |
| FORGETTING | Thinking no more of winning? In favour of coming first! (10) |
| FAINTHEART | 50% fail in the art of winning a fair lady (5,5) |
| EGOT | How the achievement of winning a Grammy, an Emmy, an Oscar and a Tony during a career in show business is known (4) |
