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This year's Super Bowl broke the tradition of using Roman numerals. According to this article the NFL postseason media guide says:

The Roman numerals were adopted to clarify any confusion that may occur because the NFL Championship Game — the Super Bowl — is played in the year following a chronologically recorded season.

But the article also points out:

But it really doesn't explain, though, why Roman numerals are used, not numbers.

In fact, for just one year, the NFL is not going use Roman numerals. Next year would have been Super Bowl L. The league reportedly went through 73 versions of a logo with the letter "L" and decided it didn't work.

The Olympics also uses Roman numerals—presumably because it connects the modern version the ancient tradition. After Super Bowl V, the numbering system was retroactively applied to I-IV, but I haven't been able to figure out why.

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An article in the Christian Science Monitor indicates that it was Lamar Hunt's idea initially:

"It was [Hunt’s] brainchild," said Moore of the numbering system in an interview with Yahoo. "I think people felt from the start that it had something to it, even if they couldn’t quite put their finger on exactly what it was. Before long it was just part of it. Now it wouldn’t be the same without it."

The article states that it specifically is not related to the Olympics, at least not directly:

"The NFL didn't model after the Olympics," Dan Masonson, director of the league's corporate communication, told the AP.

They then go on to explain that the reason for using numbers of any sort is due to what the NFL media guide explains (i.e., they want to avoid confusion if you said "2014 Superbowl" what that refers to), and that Roman Numerals were selected to make it seem more prestigious.

The Roman numerals were used to make the game seem more prestigious, back when the Super Bowl was not yet the most watched television event of the year. “It’s much more magisterial,” Moore told the AP.

Now, it's perfectly reasonable to guess that both the Olympics and the NFL have the same root reason - Roman Numerals seem fancier, of course.

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