The JFL started in the late 1980s as a simple football game between two of the Jenkins brothers, Jeff and Jim. By the early 1990s, more of the Jenkins family started getting into the action. At that point, each week involved long distance phone calls to make picks and find out what the spread and standings were, as the internet hadn't yet become mainstream.

By the mid-1990s, the electronic era was underway. The spread and standings were faxed to some players and, slowly, more and more of the players started using the new electronic-mail to submit picks and avoid the weekly phone bills. The game continued expanding as, almost each year, a new family member would join the game. The game had seen only minor changes through it's almost ten year history up until this point. This would all change in 1998.

In August of 1998, the game would transform itself with a simple web interface and a new name - the JFL, or Jenkins Football League. For the first time, non-family members would be invited to participate. As luck would have it, this first year would see a non-Jenkins family member take the Championship.

During the next few years, the JFL would continue to grow with more sophisticated, more entertaining and a more stable web portal. The game itself would see some changes also. In 1999, the "Bonus Game" would be added. This addition alone would add the most volatility and excitement to the weekly progression of teams and their points. In 1999, the game would also return to the format of including all NFL games each weekend. In 2000, the game would add another Bonus game to the weekly line-up. And in 2001, in its most ambitious expansion, the JFL would add 3 new side games - the Head-to-Head competition, Elimination and a much-anticipated PlayOffs game. The JFL would take on more of a "league" feel with the addition of team names.

The fifth year of the JFL, 2002, was its most aggressive. The 2002 season opened up with a new, dynamic website, driven by a custom JETS database management system. This allowed live picks selection for the first time in the league's history, giving JFL teams the ability to pick or change their selections up until kick-off of each game. 2002 was a phenominal expansion team year, with the number of JFL teams almost doubling to 28 teams.

2003 would bring about the most dramatic changes in the JFL, starting with the new JFL website. JFL Conferences were added, the Head-to-Head competition was brought back and a second round of Elimination games were added.

Over the next 10+ years, the JFL would see only minor changes, before the JFL went on hiatus at the start of the pandemic in 2020.