The Landmark Conference and Old Dominion Athletic Conference are pleased to announce a four-year bowl series partnership entitled the Chesapeake Challenge. The Chesapeake Bay, the natural split between the two conferences, serves as the series’ namesake.

“The ODAC is proud to announce the Chesapeake Challenge with the Landmark Conference. We look forward to helping usher in the Landmark's newest sponsored sport with a premium postseason opportunity,” explained ODAC commissioner Brad Bankston. “This partnership establishes a framework for consistent, quality postseason competition outside of NCAA Tournament play, fulfilling a long-desired goal of our programs. We are excited to share in that experience with quality schools and established football programs.”

The format of the series will feature two games with four teams (two from each conference) playing in either the Cape Henry Bowl or the Cape Charles Bowl. Cape Henry and Cape Charles serve as the northern and southern gateways of the Chesapeake Bay. Each conference will be represented by the top two teams from their respective league standings that do not qualify for the NCAA postseason.

By the time 2023 rolls around, 16 of Division III's football conference will have a postseason bowl game to play for, as well as the Division III football NCAA playoffs.

The Landmark's first season of football will be in 2023. D3sports.com originally broke the news that the Landmark was adding football in February 2022.

The Chesapeake Challenge will begin in 2023 with the No. 1 seed in the ODAC hosting the second seed from the Landmark in one bowl game, while the No. 1 seed in the Landmark will host the second seed of the ODAC in the other postseason contest. Games will be played at member campuses. The same format will be used in 2025.

“The Landmark Conference is thrilled to partner with the Old Dominion Athletic Conference for a bowl series,” said Landmark commissioner Katie Boldvich. “Securing a bowl partnership with a strong conference in our inaugural season further solidifies the conference’s commitment to the sport of football and the overall experience of our member schools and student-athletes. I look forward to watching new rivalries form and cannot wait to officially hit the gridiron in 2023.”

“I could not be more excited about this partnership with the Landmark Conference,” explained Randolph-Macon coach Pedro Arruza. “The more opportunities our players have to compete, the better. This will be an added bonus to the experience that we are all hoping to give our players. I guarantee they will be fired up about it. Other leagues have benefited from these kinds of arrangements, and I think it will definitely help our league improve.”

"The Chesapeake Bowl Challenge matchup series between the Landmark and ODAC is something we are very excited about,” said Catholic University coach Mike Gutelius. “Our football team was a member of the ODAC for a very long time and has a history of great games against many of those schools. This announcement between our two conferences is almost the best of both worlds. We will get to live in the Landmark Conference like all the other sports here at Catholic, but we will occasionally get to see some old foes from the ODAC. I think it will be a really good setup for both conferences."

The Landmark and ODAC are committed to securing neutral sites for the 2024 and 2026 series. In those years, one site will host both games.

“This is an exciting partnership with the Landmark conference,” expressed Scott Yoder, coach at Shenandoah and chair of the ODAC football coaches committee. “A high quality, postseason bowl will enhance the quality of the athletic experience for our players. I know Shenandoah is looking forward to this opportunity.”