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Discussion Starter #1 (Edited)
With all of the free time, I have created some tennis trivia questions. I think they are fairly difficult, although I may be proven wrong by some of the trivia experts on MTF. If you answer the question correctly, you can pick the next topic.

Note: Only main draw ATP matches (including Grand Slams but not including Davis Cup) from January 1st, 2000 until now are considered. If this is popular, I may create questions from challenger matches or from the 20th century.

Current Topics

Tournament Finals
Qualifiers, Wildcards, Lucky Losers and Protected Rankings
Fewest ATP Wins
Fewest ATP Losses
Matches Played while Outside the Top 100
Tennis Players by Country
Lowest Ranked Winners

Question 1: Fewest ATP Wins

Who is the only player to beat an Olympic singles gold medalist despite only winning one (1) ATP match? - Caio Zampieri in 2011 at Santiago

Question 2: ATP Players by Country

Which country has only had one player win a main tour match in the 21st century (Davis Cup not included) yet has won an ATP tournament? - Luxembourg (multiple answers)

Question 3: Tournament Finals

Many tournament finals are contested between players side by side in the rankings. A recent example is the ATP Cup final with World Number 1 Rafael Nadal playing World Number 2 Novak Djokovic. That is an example of the highest ranked side by side pair. Who are the lowest ranked side by side pair to play each other in an ATP tour final? - Mexico City 2000: Chela (128) d. Puerta (129)

Question 4: Tournament Finals (Easier)

Outside of the big 4 (Djokovic, Murray, Federer, Nadal) who has won the most ATP titles in the 21st century? - Andy Roddick with 32 titles

Question 5: Qualifiers, Wildcards, Lucky Losers and Protected Rankings (Easier)

Who is the only player in win an ATP tournament as a wildcard with a ranking in the top 5 in the world at the time? - Roger Federer (2018 Rotterdam), Novak Djokovic (2017 Eastbourne) & Wawrinka (2017 Geneva) - Problem with Data from Tennis Abstract.

Question 6: Fewest ATP Wins

Despite only having four ATP tour wins, this player never lost in the first round of a tournament. Who is he? - Matthew Barton

Question 7: Qualifiers, Wildcards, Lucky Losers and Protected Rankings (easier)

According to Tennis Abstract's data, which player has received the most wildcards in the 21st century? - James Blake

Question 8: Challenger Finals (Easier)

Who is the highest ranked player to win a challenger event in the 21st century? - Joachim Johansson (12), Luxembourg CH 2004

Question 9: Tennis by Country

Outside of the four countries that host grand slam events, which country has received the most wildcards in the 21st century? - Germany

Question 10: Tournament Finals

Who is the lowest seeded player to win an event in the 21st century? - Ivan Ljubicic (Indian Wells 2010), and Albert Costa (RG 2002)

Question 11: Qualifiers, Wildcards, Lucky Losers and Protected Rankings

What player has entered the main draw of an ATP event (including slams) as a qualifier the most number of times in the 21st century? - Alejandro Falla (42 times)

Question 12: Matches Played Outside the Top 100

Who is the only player to win two completed matches (no retirement or walkover) against top 5 opponents while ranked outside the top 100? - Marin Cilic

Bonus: There is a second player who won two matches over top 5 players while ranked outside the top 100, but this second player does not meet the requirement of completed matches. Who is this player? - Chris Guccione

Question 13 - Tournament Finals

Which two players played in the final is the biggest gap in rankings where the higher ranked player won? - 2009 s-Hertogenbosch final, Benjamin Becker (82) d. Raemon Sluiter (866)

Question 14: Qualifiers, Wildcards, Lucky Losers and Protected Rankings

What is the largest gap in the rankings in a match when a wildcard beat another player?

Question 15: Fewest ATP Wins

Despite only winning one ATP match in the 21st century, he beat a player ranked in the top 5.
 

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Viola
 

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Discussion Starter #5
Beat murray...and has 1 ATP win lol
You are correct that he did beat Murray (in a challenger) and he has at least 1 ATP, but not only 1 ATP win. :)

As noted in post 1, only ATP main draw matches are included since the year 2000. No challengers, no Davis Cup. Viola did beat Murray in a challenger and he has won 4 career ATP matches.
 

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Paul Baccanello defeating Marc Rosset in Bangkok 2004 - assuming Grand Slams don't count, were he has one more win.

Not that I knew about it before, but was a lot of fun searching for it and looking at all these players that beat Kafelnikov, Massu, Rosset and Agassi. :)

I encountered Nenad Zemonjc on that journey, which is also an interesting one. Has only four Singles ATP wins and one of them was against Agassi, another one against Kiefer. Not the worst to beat.
 

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Discussion Starter #7
Paul Baccanello defeating Marc Rosset in Bangkok 2004 - assuming Grand Slams don't count, were he has one more win.

Not that I knew about it before, but was a lot of fun searching for it and looking at all these players that beat Kafelnikov, Massu, Rosset and Agassi. :)

I encountered Nenad Zemonjc on that journey, which is also an interesting one. Has only four Singles ATP wins and one of them was against Agassi, another one against Kiefer. Not the worst to beat.
What a great answer! However, not the answer I was hoping for. I did include grand slams as ATP Tour matches despite them being ITFs so I had Paul Baccanello at two wins. I have since tried to clarify the initial post. The only main draw main tour matches I didn't consider are Davis Cup matches. Since you were right as GS events are ITF events you can pick a topic for the next question.

Current Topics

Tournament Finals
Qualifiers and Wildcards
Fewest ATP Wins
Fewest ATP Losses
Matches Played while Outside the Top 100
Tennis Players by Country

However, there is still a player with only one career ATP win that got it over an Olympic gold medalist, so feel free to try to figure out who he was.

I love what you noticed about Zimonjic. That is one thing I really like going back and looking at historical players.
 

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Discussion Starter #9
Active Questions

Question 1: Fewest ATP Wins

Who is the only player to beat an Olympic singles gold medalist despite only winning one (1) ATP match?

Question 2: ATP Players by Country

Which country has only had one player win a main tour match in the 21st century (Davis Cup not included) yet has won an ATP tournament?
 

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Question 1: Caio Zampieri beating Marcelo Rios in Santiago 2011 - not sure, how I overlooked him in my first search, should be easier than Baccanello :D
 

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Discussion Starter #12
Question 2: Luxembourg (Gilles Muller)?
Correct. I should note, there are at least two correct answers to this question.

Current Topics

Tournament Finals
Qualifiers and Wildcards
Fewest ATP Wins
Fewest ATP Losses
Matches Played while Outside the Top 100
Tennis Players by Country

I will be out for a bit on a long walk so I will post when I am home.
 

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Discussion Starter #15
Question 3: Tournament Finals

Many tournament finals are contested between players side by side in the rankings. A recent example is the ATP Cup final with World Number 1 Rafael Nadal playing World Number 2 Novak Djokovic. That is an example of the highest ranked side by side pair. Who are the lowest ranked side by side pair to play each other in an ATP tour final?
 

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Discussion Starter #17
These questions are way beyond the pay grade of the average MTFer... ;)
Glad to hear. Want to make people have to try hard. I'll give you an easier one. :)

Question 4: Tournament Finals

Outside of the big 4 (Djokovic, Murray, Federer, Nadal) who has won the most ATP titles in the 21st century?
 

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Question 3: Tournament Finals

Many tournament finals are contested between players side by side in the rankings. A recent example is the ATP Cup final with World Number 1 Rafael Nadal playing World Number 2 Novak Djokovic. That is an example of the highest ranked side by side pair. Who are the lowest ranked side by side pair to play each other in an ATP tour final?
No idea, but maybe opelka vs schnur?
 

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Discussion Starter #20
Singles? Roddick?
This is correct! Andy Roddick has won 32 ATP events in the 21st century.

I've decided we can do two questions at once. One that is a bit easier like this one and one that is tough like Question 3. Did you want to pick the topic of the next question?

Current Topics

Tournament Finals
Qualifiers, Wildcards, Lucky Losers and Protected Rankings
Fewest ATP Wins
Fewest ATP Losses
Matches Played while Outside the Top 100
Tennis Players by Country
Lowest Ranked Winners
 
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