Copper jacket rifle bullets, like yours on the left, started being mass produced around 1900 - your lead bullet on the right started being produced mid to late 1880's.
Both are fairly modern. The jacked bullet may be older than the lead. The lead bullet is cannelured, ridges in the grooves. Real old bullets didn't have that. Tony
Both are fairly modern. The one on the left is definetly a modern high powered rifle bullet and the the other has the crimping and or ridges on it which tells you it's also a modern bullet. Given some dimensions calibers could be determined.
The lead one without measurements looks like a .45 caliber long colt, and the rifle bullet looks like 30-06, at first I thought military, but looking closer it looks like there is a lead tip showing on the bullet. With measurements, could be a lot of other calibers.