The Flyers won all four games and were the more experienced team during this era; having played with the "non-scholarship" restriction for nine seasons prior to Drake's decision.

They would end up joining with coaches from three other institutions (and later a fourth) to form the Pioneer Football League.

[10] The initial meeting between the rivals as members of the Pioneer Football League occurred on October 23, 1993.

The Bulldogs defeated the Flyers 34–23 in Des Moines on October 21, 1995[12] for their first series victory, leading to their first Pioneer Football League title.

"[16] Dayton won the next year at Welcome Stadium prior to a Drake three game streak which included the biggest upset in the series in 2015.

On November 21, 2015, the Flyers came into Des Moines undefeated (10–0) in college football playing for NCAA Division I FCS playoff positioning.

In a press conference before the game Flyer senior offensive lineman Zac Morgan indicated "we’re playing a good Drake team, which we’ve had problems with in the past.

"[17] The Bulldogs would lead 21–0 at halftime and withstand a Dayton rally in the second half to prevail 27–17 on a snowy Iowa day.

"[18] The Flyers would get revenge winning the next two seasons 35–10 and 20–10 before the Bulldogs picked up an eleven-point 2018 victory in Ohio.

[19] Dayton won the 2019 game 46–29 in Des Moines[20] prior to the series being interrupted due to the COVID-19 pandemic.