Sometimes, it does matter.
For example, with the Cadillac Northstar engines (at least the FWD versions), if you filled the sump (which is 7.5-8 quarts) to the full level cold, and you went to measure it hot, you'd be "overfilled" by about half a quart. Folks would complain about excessive oil usage because they kept topping the oil off cold. When recommended to keep the oil at the full line, WHEN HOT, oil usage would suddenly not be there anymore. Full when hot is typically about half a quart "low" when cold.
As noted above, it just depends on how the dipstick is calibrated. I'm sure larger volume sumps experience this effect more, due to the extra volume of oil that does expand.
For example, with the Cadillac Northstar engines (at least the FWD versions), if you filled the sump (which is 7.5-8 quarts) to the full level cold, and you went to measure it hot, you'd be "overfilled" by about half a quart. Folks would complain about excessive oil usage because they kept topping the oil off cold. When recommended to keep the oil at the full line, WHEN HOT, oil usage would suddenly not be there anymore. Full when hot is typically about half a quart "low" when cold.
As noted above, it just depends on how the dipstick is calibrated. I'm sure larger volume sumps experience this effect more, due to the extra volume of oil that does expand.