Green’s Dictionary of Slang

1. to deprive of money [bleed v.¹ (1)].

1884

H. Smart Post to Finish II 155: ‘He is very likely to want a thousand pounds at any moment. There’s a leaven of the old squire in his composition, and I recollect hearing that he was blooded over the Phaeton Leger.’ ‘You surely can’t mean that he has taken to racing? Why, you must be aware that he has no money for anything of that sort.’.

2. (Aus., also bloody) to cause to bleed [SE blood].

1937		C. Pifer ‘Executioner’ in All-America Sports Mag. Jan. 🌐 He didn’t have no stomach to go bloodin’ folks.
1967		F. Salas Tattoo the Wicked Cross (1981) 208: Beat on the punk, / knock him around, / bloody him up, / make him bawl like a broke-dick-dog.

3. to initiate into a gang by a form of blood-letting ritual.

2000

Guardian Rev. 28 Jan. 11: Later when the big lads were blooding me into their gang, they held Squirrel down so I could give him a kicking.