Alright so I have only just managed to spot this one, but I have had this issue on a server as old as Spigot 1.8.8. But since I always assumed it was a Vanilla bug I never bothered reporting it.
How to recreate it.
You need a server that is Spigot based with a ping higher than 200MS.
In Vanilla (1.11): https://img.ssamjh.nz/i/k7jh5.mp4
In Spigot (1.11 - git-Spigot-16c940b-eed13ca): https://img.ssamjh.nz/i/xq9ng.mp4