| | 1995 Film | | | 
Real dates. Fictional events. | 16 |  |
| - 1994
- January
- January 7
- Billy Madison 1995 Film | Source Timeline
 - Because his father paid off his teachers to give him good grades, Billy pledges to go back and complete first grade through twelfth grade all over again, each grade in two weeks, take the test and re-graduate to prove to his father he's not an idiot so he can take over Madison Hotels.
- May 6
- Billy Madison 1995 Film | Source Timeline
 - After being blackmailed by Eric, Principal Anderson of Polly Fector Elementary announces at a press conference that Billy paid him a $5,000 bribe to let him pass. Billy drops out of high school.
- May 13
- Billy Madison 1995 Film | Source Timeline
 - Billy and Eric go mano y mano - an academic decathlon: one day, 10 events, testing all the knowledge one would gain in high school. Also, the O'Doyle family dies in a tragic accident when their station wagon slips on a banana peel, drives off a cliff and explodes.
- June
- June 15
- Billy Madison 1995 Film | Source Timeline
 - Original date that Billy was supposed to finish completing first grade through twelfth grade all over again in order to be able to take over Madison Hotels, before Eric blackmailed Principal Anderson to lie about Billy paying him a bribe, causing Billy to drop out of high school.
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Fictional business and products... and more | 9 |  |
| |  | 5 | |
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