In 1904, Fred Coleman won a match with Fen Cooper; 50 Live Birds, 21 yd. rise, one shot only, gun below elbow until bird is on wing, $500 a side (about $12,500)
https://digital.la84.org/digital/collection/p17103coll17/id/38024/rec/29

[Linked Image from photos.smugmug.com]

Thread regarding Coleman
https://www.trapshooters.com/threads/fred-coleman.829581/