This pic is, I think, a reference to the so-called "Mid Night" team (often called the Midnight Club in English sources), a group of (illegal) street racers said to be active during the 80s and 90s on the Wangan Route on the Shuto Expressway in Tokyo. Their cars were extensively modified for speed and were purportedly able to achieve speeds exceeding 300 kmph (200 mph). Tales of the club's exploits inspired many fictional stories like Wangan Midnight and the Midnight Club series of games.
The thigh stamp and shorts/jacket print of the original umagirls above are also styled after the stickers and decals purportedly used by the Midnight Club members.
Trying to find reliable info about this group is tricky though. There are many articles written about them, but nearly all of them are in English, and they usually cite some "unidentified source" or "former member of the Midnight Club who wishes to remain anonymous", which is... sketchy. There's also at least one "journalist" who was caught making stuff up for the now-removed Wikipedia article. Trying to look up "Mid Night" and "racing" on the Japanese interwebs just turns up results on Wangan Midnight and the various Midnight Club games.
I highly doubt that the games were based off fabricated Western accounts. Probably real illegal Japanese street racing inspired the games which in turn resulted in the highly exaggerated Western writeups that confused reality with the game plots. Perhaps some of the anonymous sources were actually from friend groups that gathered in the arcades to play the games.