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1.Delaware or Virginia?
Delaware
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Virginia
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Delaware was the first state, ratifying the Constitution on December 7th, 1787. Virginia joined on June 25th, 1788.
2.Louisiana or Florida?
Louisiana
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Florida
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Louisiana: April 30th, 1812; Florida: March 3rd, 1845
3.Illinois or Kentucky?
Illinois
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Kentucky
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Illinois: December 3rd, 1818; Kentucky: June 1st, 1792
4.Minnesota or Montana?
Minnesota
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Montana
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Minnesota: May 11th,1858; Montana: November 8th, 1889
5.California or Texas?
California
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Texas
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California: September 9th, 1850, during the Gold Rush; Texas: December 29th,1845, right before the Mexican-American War
6.Arizona or Colorado?
Arizona
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Colorado
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Arizona: February 14th, 1912; Colorado: August 1st, 1876, known as the Centennial State since it entered the Union 100 years after independence
7.Alaska or Hawaii?
Alaska
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Hawaii
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These were the last two states to join the Union, with Alaska joining on January 3rd, 1959 and Hawaii on August 21st, 1959
8.Vermont or Massachusetts?
Vermont
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Massachusetts
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Vermont: March 4th, 1791, becoming the first state that wasn't part of the 13 original colonies; Massachusetts: February 6th, 1788
9.West Virginia or Tennessee?
West Virginia
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Tennessee
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West Virginia: June 20th, 1863, as a secession from Virginia during the Civil War; Tennessee: June 21st, 1796
10.Oklahoma or Kansas?
Oklahoma
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Kansas
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Oklahoma: November 16th, 1907, its late admission reflecting the fact that it was mostly Indian Territory; Kansas: January 29th, 1861, right before the Civil War
11.Missouri or Iowa?
Missouri
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Iowa
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Missouri: August 10th, 1821, admitted as part of the Missouri Compromise; Iowa: December 28th, 1846
12.Washington or Oregon?
Washington
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Oregon
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Oregon: February 14th, 1859; Washington: November 11th, 1889
13.Pennsylvania or Ohio?
Pennsylvania
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Ohio
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Pennsylvania: December 12th,1787; Ohio: March 1st, 1803
14.Wyoming or Wisconsin?
Wyoming
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Wisconsin
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Wyoming: July 10th, 1890; Wisconsin: May 29th, 1848
15.Alabama or Georgia?
Alabama
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Georgia
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Alabama: December 14th, 1819; Georgia: January 2nd, 1788
Glad you liked it! That's definitely the trend for most states. I didn't want it to be that obvious though so I tried added a few tricky ones that went against that rule, like Louisiana and Florida.
Yeah, generally when people talk about the date a state being accepted into the Union, it's the date where it first happened, not the date they re-entered (for Confederate States). Keep in mind the Union never really saw the Confederacy as a legitimate entity--the process of "re-entering" the Union was more a formality than an actual expansion of the Union.