Richard died suddenly on Thursday at the age of 54, with the club announcing details of his passing earlier today.
Upset ex-players and former club chairman John Ryan are among those to have paid tribute to Mr Bailey, who worked for the club for 30 years, many of them alongside his wife Clare who also works for Rovers.
Mr Ryan described the death as an ‘absolute tragedy.’
Paying tribute on Facebook, he wrote: “So sorry to hear the news - an absolute tradgedy for someone so young and full of life. My most sincere condolences Clare and family RIP Xx.”
Defender James O’Connor, who played more than 200 games for Rovers between 2006 and 2012 said: “Absolutely shocked and heartbroken to hear of the passing of one of the nicest fellas I’ve ever met.
“In my six years at Rovers, I never saw Richard without a kind word to say and a smile on his face.
“An absolute gentleman who will be sadly missed.
“All my love and thoughts to you and the family Clare.”
Former goalkeeper Jan Budtz wrote: “So sorry for your loss Clare – my thoughts are with you and James, your Rovers family will always be here for support.”
Ian Duerden, a striker at the club in the late 90s and early 2000s, posted: “Sorry for your loss,” while Nick Limber, who played for the club in the early 90s added: “So sorry to hear this very sad news Claire. Our thoughts are with you and the family.”
Liam Wakefield, who played at Rovers until 2015 wrote: “So, so sorry for your loss, thinking of you all.”
Doncaster Rovers’ super fan Paul Mayfield, known to supporters for his trademark gnome, also paid tribute, saying: “From everyone connected with Rovers Supporters Club we send our love and thoughts.
"Richard was one of the nicest, caring and thoughtful person you could wish to meet - nothing too much for him, loved my so many, missed by so much more.
"We all had a great weekend in Blackpool with you just two weeks ago. Richard let his hair down and loved it.”
“RIP Richard top man.”
Richard began working in Doncaster Rovers’ Football in the Community in the early 1990s, initially as a community coach in schools.
He progressed through the ranks to become a community officer, overseeing the schools programme while Football in the Community evolved into the Foundation.
He played a key role in establishing girls football within the club’s community programme alongside Eric Randerson.
Latterly, Richard held the title of health and wellbeing officer within the Foundation.
He continued to work for the club as an ambassador, guiding group experiences and, in particular, matchday mascots, for whom he provided in-depth tours of the Eco-Power Stadium.
Club Doncaster chief operating officer Shaun Lockwood said: "This is a truly sad loss. We have lost one of our own.
"Richard was a wonderful person and someone who has been synonymous with Doncaster Rovers for more than 30 years.
"Our thoughts are with his family and friends, as colleagues and supporters alike share our condolences."