The Dean Court favourites, who both received international caps during distinguished professional careers, will represent the Tatnam club in cameo roles against Stephen Purches's development squad.
Dorset legend Richardson, 47, will bring down the curtain on his remarkable playing career after making more than 1,000 semi-professional appearances following his appointment as Dolphins first-team coach.
Left-back Cummings worked with Richardson during his spell with Poole last season before the former Scotland international linked up with ex-Cherries boss Lee Bradbury at Conference South club Havant and Waterlooville.
Anderton, capped 30 times for England, featured for Cherries between 2006 and 2008 before he retired from professional football at the age of 36.
Richardson is also optimistic that QPR hot shot and Poole poster boy Charlie Austin will be present, albeit purely on a watching brief, to meet with supporters at the highly-anticipated showpiece.
Meanwhile, Dolphins manager Tom Killick received a boost ahead of his side's first pre-season friendly after Marvin Brooks committed his future to the club.
The 24-year-old midfielder had been on trial with full-time Conference South outfit Sutton United but this week expressed concerns over clashes with his work as a personal trainer.
Brooks, who had promised not to join any other part-time club, signed his one-year deal with Poole yesterday.
Admission for Richardson's testimonial is set at £7 for adults, £5 for concessions and £1 for under-16s.