Cummings (10-0) will be making his Strikeforce debut on the card. Kennedy (10-2) made his organization debut in June, defeating Nick Thompson via submission. The fight will be contested at 185 pounds.
Strikeforce Challengers airs Friday, September 25 on Showtime from the SpiritBank Event Center in Bixby, Okla.
Cummings was once rumored to be facing Paul Bradley on the card. His most famous win is a split decision victory over veteran Terry Martin at XFC: Rumble in Racetown 1 in February.
Kennedy recently accepted an offer to serve in the Texas National Guard after spending six years in The United States Army, the last three as a sniper in the Seventh Special Forces Group.
No other bouts have been officially announced.