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New American Oxford Dictionary

losingest

los ing est |ˈlo͞oziNGist ˈluzɪŋɪst | ▶adjective informal losing more often than others of its kind; least successful.

 

Oxford Dictionary

losingest

losingest |ˈluːzɪŋɪst | ▶adjective N. Amer. informal losing more often than others of its kind; least successful: the losingest club in baseball history.