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Wearing a yarmulke is a minhag. Not putting a stumbling block is d'oreisa.

Yet, I have noticed that Torah observant boys and young men play sports like basketball, flag football, and soccer with yarmulkes, even though there is a very good chance that they will fall off and cause someone to trip.

Is it assur to play sports with a yarmulke?

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not according to the Taz 8:3 –  sam Nov 18 '13 at 0:31
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Under circumstances where it would be dangerous to play sports while wearing a yarmulke, i.e. where it is likely to fall and trip someone, it's obvious that one may not do so. However, this doesn't generally seem like a realistic scenario. –  Fred Nov 18 '13 at 0:51
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puting aside the discussion of whether there is "a very good chance that they will fall off and cause someone to trip", there is also a discussion whether the prohibition of placing a stumbling block is actually referring to a physical stumbling block, see here (and linked questions): judaism.stackexchange.com/questions/16772/… –  Menachem Nov 18 '13 at 1:41
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@Fred: "it's obvious one may not do so". Play sports or wear the Yarmulke? –  Gershon Gold Nov 18 '13 at 2:21
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I don't think the danger of tripping over someone's yarmulke is the biggest danger athletes face... –  Ariel K Nov 18 '13 at 3:21
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1 Answer

Many who play attach their Yarmulkas via a bobby pin or Kippon. This assures that it will remain on their head and not fall off while playing sports.

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+1. A good idea, though they are not effective for all types of hair under all circumstances. –  Fred Nov 18 '13 at 2:28
    
"assures" more likely "mitigates the risk" –  Double AA Nov 18 '13 at 2:29
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