There's too many things it depends on to make a guess for sure, like what time limit are you playing and when they get online. But maybe just divide the number of total members of chess.com by how many games you've played to see what percent of members you have already played, then that would be the percent chance of a random match giving you someone you already have
What are the odds of randomly playing the same person twice?
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I had it happen to me 5 times 
Once you get in the higher percentiles it becomes noticeable that you are bumping into players you have previously played against. With a rating around 1200 you will rarely meet the same opponent twice.
Jul 17, 2023
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#10
Depends on the elo. Bare in mind I’m only 1800 and that’s still down to just 100,000 players. Not all of them are active or within the rating range
Jul 17, 2023
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#12
X = (1/number of members within 200 rating points) X number of games you play. The number of members within 200 points is many millions if you’re rated 750, so us middling players are unlikely to get a rematch. But if you’re 2600, the denominator is very low and you’re likely to get repeat matches.
Bro I swear this has happened to me before with the same guy popping up at least 4 times
You might play the same person if you play chess960 since there are not many players that play that format
Aug 8, 2023
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#15
micahwchess wrote:
What are the odds of randomly playing the same person twice?
Maybe 4?
Aug 8, 2023
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#16
Depends which level you’re at. At 600? Very low cos there’s millions of players. At 1200? Probably relatively unlikely. I’m 1800, I’ve paired with a couple of people multiple times cos there’s only a few tens of thousands. At master level it happens all the time 🤷♂️
Aug 8, 2023
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#18
Unicorn_Horn12 wrote:
micahwchess wrote:
What are the odds of randomly playing the same person twice?
Maybe 4?
4 what
Aug 8, 2023
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#19
Siiiiiiike wrote:
Unicorn_Horn12 wrote:
micahwchess wrote:
What are the odds of randomly playing the same person twice?
Maybe 4?
4 what
Ok, let me guess again... 5?
What are the odds of randomly playing the same person twice?