Found all three of these really close together today. All are deformed in one way or another. their total wieght is 131.25 grains so im guessing roughly 43 - 44 grains each.
Im thinking their from early 20th century but want your info
dime is for size comparision
Without exact measurements it's hard to tell anything. However the grease grooves on your bullets are textured, which dates them no earlier that the 1890's forward.
Measure the width of the bottom of the bullet in millimeters, with that measurement you could find out the caliber by using this "Millimeter to Caliber" converter.
A US dime's diameter is .705-inch. Your fired bullets are somewhat mis-shapened by impact damage, but comparing the diameter of their undamaged bottoms with the dime in your photo indicates they are .32-caliber. They look like the same bullet discussed in the What-Is-It? last week, here: http://www.treasurenet.com/forums/what/439335-help-identifying-old-one-ringer-bullet.html
I tend to agree with Charlie P.'s suggestion in that discussion that they are .32 ACP (Automatic Colt Pistol) bullets. He posted a photo of a box of .32 ACP bullets showing some of them outside of the box. Please check the discussion at the link above.
According to The Cartridge Collector website, the first lead-bodied bullets which had a "reeded" body-groove (which is also called a knurled cannelure) were made in 1877.
Here's a photo of a .32 bullet (with dime for comparison) which I think matches your bullets.