They had separate opponents and were playing different games.

The two men were not playing each other.
 
Riddle Masters 29.11.2023

Good morning Riddle Masters! 😊

It’s time to get your brain working with our second riddle of the week!

Two men were playing tennis. They played five sets, and each man won three sets. How can this be possible?

Oooh, is it just me, or is this one particularly tricky? I’m sure you lot will unlock the answer. And when you do, make sure to post your answer in the comments below.

As always, our ‘spoiler’ button will automatically hide your and others’ answers. To reveal those answers, simply click the ‘spoiler button’.

Good luck and Happy Riddle-ing! ;)
They were not playing agianst each other. They were playing 2 different games
 
They were not playing against each other, maybe playing against women
 
The 2 men were on the same doubles team.
Or.... each man was playing against a different opponent in different games.
 
Riddle Masters 29.11.2023

Good morning Riddle Masters! 😊

It’s time to get your brain working with our second riddle of the week!

Two men were playing tennis. They played five sets, and each man won three sets. How can this be possible?

Oooh, is it just me, or is this one particularly tricky? I’m sure you lot will unlock the answer. And when you do, make sure to post your answer in the comments below.

As always, our ‘spoiler’ button will automatically hide your and others’ answers. To reveal those answers, simply click the ‘spoiler button’.

Good luck and Happy Riddle-ing! ;)
They were playing in different matches
 
Riddle Masters 29.11.2023

Good morning Riddle Masters! 😊

It’s time to get your brain working with our second riddle of the week!

Two men were playing tennis. They played five sets, and each man won three sets. How can this be possible?

Oooh, is it just me, or is this one particularly tricky? I’m sure you lot will unlock the answer. And when you do, make sure to post your answer in the comments below.

As always, our ‘spoiler’ button will automatically hide your and others’ answers. To reveal those answers, simply click the ‘spoiler button’.

Good luck and Happy Riddle-ing! ;)
Both men were partners playing another 2 men, Nan.
 
Riddle Masters 29.11.2023

Good morning Riddle Masters! 😊

It’s time to get your brain working with our second riddle of the week!

Two men were playing tennis. They played five sets, and each man won three sets. How can this be possible?

Oooh, is it just me, or is this one particularly tricky? I’m sure you lot will unlock the answer. And when you do, make sure to post your answer in the comments below.

As always, our ‘spoiler’ button will automatically hide your and others’ answers. To reveal those answers, simply click the ‘spoiler button’.

Good luck and Happy Riddle-ing! ;)
They were playing doubles against another two people
 
Riddle Masters 29.11.2023

Good morning Riddle Masters! 😊

It’s time to get your brain working with our second riddle of the week!

Two men were playing tennis. They played five sets, and each man won three sets. How can this be possible?

Oooh, is it just me, or is this one particularly tricky? I’m sure you lot will unlock the answer. And when you do, make sure to post your answer in the comments below.

As always, our ‘spoiler’ button will automatically hide your and others’ answers. To reveal those answers, simply click the ‘spoiler button’.

Good luck and Happy Riddle-ing! ;)
They were both on the same side in a doubles match.
 

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