TennisRungs.com (https://info.tennisrungs.com/) is an online tennis ladder used by the Fort Green Tennis Assocation (http://www.fortgreenetennis.org/). In 2017, over 150 folks competed in two ladders managed by the FGTA. As time progressed, I became frustrated by feature limitations with the ladder software. In paticular, it was very difficult to challenge players ahead of me since a player could only be challenged by one person at a time. Since everyone wanted to challenge the players near the top of the ladder, it was rare for those top players to be avilable for challenge.
I built a hack that allowed me to automatically challenge players of my choosings -- as soon as they became available to be challenged. The hack was written with a simply python script. It utilized a phantom headless browser to log in to the site on a configurable schedule, check the availability of a configurable list of players, and challenge any that were available.
The hack worked like a charm. I was able to challenge players in the top 20, win those matches, and finish in the top 10 at the end of the season. I did feel sort of guilty about gaining an unfair advantage in the ladder, so I made it publicly known what I was doing and offered to run the hack for anyone else that requested it. Furthermore, after I took over running the ladder for the winter season, I obviously had to cease using the hack. So it's on the shelf, for now (and until the 2018 summer sesason gets under way!