Winning can mean different things to different people. For some, winning is about coming out on top in a game or competition. For others, it’s more about achieving a personal goal or overcoming a challenge. Regardless of how you define it, winning often requires determination, effort, skill and maybe even a little bit of luck.
Riddles can be a fun way to get your brain working and challenge yourself to think in new ways. This collection of winning riddles runs the gamut from sports and games to personal victories. Some may require outside-the-box thinking to solve. Others have clever plays on words that hint at the answer. How many can you get right? Keep reading to find out!
Riddles about games and competitions
Here are some brain teasers about coming out on top in various games and contests:
Riddle 1
I have kings and queens, but no subjects. I have spaces, but no room. What am I?
Answer: A chessboard
Riddle 2
We’re five little objects of an everyday sort; you’ll find us all in a tennis court. What are we?
Answer: Vowels A E I O U
Riddle 3
I can be cracked, made, told, and played. What am I?
Answer: A joke
Riddle 4
I have four legs but no feet. I can rotate 360 degrees. Man has raced me for centuries. What am I?
Answer: A wheel/bicycle
Riddle 5
I’m where yesterday follows today, and tomorrow is in the middle. What am I?
Answer: A dictionary
Riddle 6
What has a head, a tail, is brown, and has no legs?
Answer: A penny
Riddle 7
What can you catch but not throw?
Answer: A cold
Riddle 8
What has hands but can’t clap?
Answer: A clock
Riddle 9
What gets wetter the more it dries?
Answer: A towel
Riddle 10
What has a neck but no head?
Answer: A bottle
Riddle 11
What has teeth but cannot bite?
Answer: A comb
Riddles about personal victories
These riddles are all about achieving goals and conquering challenges:
Riddle 12
The more you take away, the more I become. What am I?
Answer: A hole
Riddle 13
I am not alive but I grow; I don’t have lungs but I need air; I don’t have a mouth but water kills me. What am I?
Answer: Fire
Riddle 14
I make you weak at the worst of all times. I keep you safe, I keep you fine. I make your hands sweat, and your heart grow cold, I visit the weak, but seldom the bold. What am I?
Answer: Fear
Riddle 15
The more it dries, the wetter it gets. What is it?
Answer: A towel
Riddle 16
What always ends everything?
Answer: The letter G
Riddle 17
What gets broken without being held?
Answer: A promise
Riddle 18
What goes up but never comes down?
Answer: Your age
Riddle 19
The more you take, the more you leave behind. What am I?
Answer: Footsteps
Riddle 20
What can travel around the world while staying in a corner?
Answer: A stamp
Sports and game winning riddles
Test your sporting knowledge with these riddles:
Riddle 21
What has 18 legs and catches flies?
Answer: A baseball team
Riddle 22
What bounces higher than a skyscraper?
Answer: A basketball
Riddle 23
What has no beginning, end, or middle?
Answer: A doughnut/bagel
Riddle 24
What has a head, a tail, but no body?
Answer: A coin
Riddle 25
What gets wetter as it dries?
Answer: A towel
Riddle 26
What has a neck but no head?
Answer: A bottle
Riddle 27
What goes up and down but doesn’t move?
Answer: Stairs
Riddle 28
What has four wheels and flies?
Answer: A garbage truck
Riddle 29
What has one head, one foot and four legs?
Answer: A bed
Riddle 30
What has hands but can’t clap?
Answer: A clock
Riddles about winning money/prizes
Everyone loves to win, especially when prizes are up for grabs! Try these riddles:
Riddle 31
What has a head and a tail but no body?
Answer: A coin
Riddle 32
I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
Answer: A map
Riddle 33
What is full of holes but still holds water?
Answer: A sponge
Riddle 34
I have branches, but no fruit, trunk or leaves. What am I?
Answer: A bank
Riddle 35
What has one eye but can’t see?
Answer: A needle
Riddle 36
I have a face and two hands, but no arms or legs. What am I?
Answer: A clock
Riddle 37
What goes up but never comes down?
Answer: Your age
Riddle 38
What gets wetter the more it dries?
Answer: A towel
Riddle 39
What has a head, a tail, is brown, and has no legs?
Answer: A penny
Riddle 40
What has teeth but can’t bite?
Answer: A comb
Riddles about winning against challenges
These brain teasers focus on overcoming adversity and accomplishing goals:
Riddle 41
What belongs to you but others use it more than you do?
Answer: Your name
Riddle 42
The more you take, the more you leave behind. What am I?
Answer: Footsteps
Riddle 43
I’m light as a feather, yet the strongest person can’t hold me for more than 5 minutes. What am I?
Answer: Breath
Riddle 44
I am born in fear, raised in truth, and I come of age with lies. What am I?
Answer: Knowledge
Riddle 45
The more there is, the less you see. What could I be?
Answer: Darkness
Riddle 46
If you break me I do not stop working, if you touch me I may be snared, if you lose me nothing will matter. What am I?
Answer: Your heart
Riddle 47
I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
Answer: A map
Riddle 48
What gets broken without being held?
Answer: A promise
Riddle 49
What goes through cities and fields, but never moves?
Answer: A road
Riddle 50
What can fill a room but takes up no space?
Answer: Light
Riddles about relationships and connections
Relationships and human connections involve their own victories and challenges. See if you can solve these riddles:
Riddle 51
What belongs to you, but other people use it more than you?
Answer: Your name
Riddle 52
People make me, save me, change me, raise me. What am I?
Answer: Money
Riddle 53
What gets broken without being held?
Answer: A promise
Riddle 54
What is yours but used more by others?
Answer: Your name
Riddle 55
What is always in front of you but can’t be seen?
Answer: The future
Riddle 56
Where does today come before yesterday?
Answer: In the dictionary
Riddle 57
What can travel around the world while staying in a corner?
Answer: A stamp
Riddle 58
What gets broken without being held?
Answer: A promise
Riddle 59
What has a head, a tail, is brown, and has no legs?
Answer: A penny
Conclusion
How did you do with these winning riddles? Some probably took a bit more creative thinking than others. Riddles are a fun exercise to stretch your mind and look at things in new ways. They encourage us to move past our initial assumptions and turn ideas upside down and inside out until we find the solution.
In life, achieving goals and overcoming obstacles often requires determination mixed with flexibility. Like riddles, you may need to try different approaches and perspectives before hitting on the right formula. Whether it’s becoming a better athlete, learning a new skill, solving a work challenge or improving a relationship, winning takes effort but feels great when you get there.
