Can you sell the same player to a club and buy him back?
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@progig Hello!
Rule number 7 of OSM terms which can be found at this link state:
7.You may not buy and/or sell players for the purposes of artificially giving another manager in your league money, this makes for unfair competition.
I don't think you can do that, unless, your friend has a different IP than yours and you guys don't trade players with each other under some very cheap amounts which would clearly give you all an advantage against the other players.