So I have spent the morning doing a bit of research in order to answer your question. This practice is called "odd pricing" and it is used as a psychological tactic. Even though $4.99 is closer to $5 consumers will still tend to round down in their head, thinking they are only paying $4. People focus on the dollar component rather than the cent component, retailers realized this so they raised the cent component as high as they can while still keeping to the "odd pricing" tactic.
Now as far as I can tell their is not any evidence that this tactic was used in America before the late 1800's. There is some evidence from newspaper advertisements that the practice was put into use in the 1880's in order to have an edge over the competition. E.g Melville Stone with the Chicago Daily News.
More likely the reason, it was implemented in order to reduce employee theft. Employees would have to give change back to the customer and therefore would need to open the register, leaving a record of the sale. They wouldn't be able to just pocket the bills without having any record of the transaction.
As far as the other half of your question, I honestly do not know if there was an equivalent in Roman times, but I doubt it. Roman coins were based off the amount of gold/silver/bronze in the actual coin itself and was done through a weight exchange.
Anyways here are some sources to read if you want to:
"The Armchair Economist" by Steven E. Landburg - sorry no link
As a follow-up question, how were (or were?) pricing practices similarly affected in places with non-decimal currencies, e.g. the penny/shilling/pound system formerly used in the U.K.?
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