Flags at the Riverside Stadium have been lowered as a mark of respect for Rolando, who died suddenly at his home in Edinburgh on Thursday morning, having suffered suspected heart failure.
Renowned as a colourful character on and off the pitch, Rolando joined Boro from Celtic for a £7,000 fee in 1948.
The son of Italians who moved to Glasgow when he was aged one, Rolando quickly established himself as a popular keeper with both players and fans.
Nicknamed "The Cat" or simply "Ugo", he made his debut against Chelsea in 1948-9 season and was the club's regular goalie over the next nine years. Agile, fit and a very good keeper, his theatrical style was the talk of Ayresome Park.
A noted dressing room prankster, team-mate Brian Clough remembered him as a bubbly chap, "the sort of character that every club needs".
Rolando's widow, Irene, said he always followed the club's fortunes closely and had told her about Boro's win over Birmingham City on Tuesday night.
"Middlesbrough was Rolando's club," she said. "He was very proud of the club and everyone was always very kind to us whenever we came down.
"He was one of the last of the team he played in and he loved Middlesbrough and loved coming down and seeing everyone and we're very grateful for all that the club did for us.
"He's had a great life and he loved his sport and in particular his golf, although he wasn't able to play anymore.
"He never got to his 90th birthday in June and we had his party all planned out. Unfortunately in the last couple of years he had to close down and he was no longer able to drive.
"He hadn't been feeling very well but he had a very quick death so he didn't suffer. He was very happy about Boro winning the other day. He always looked for their scores."
Rolando played a total of 335 games for Boro, making the goalkeeper's jersey his own for eight seasons. His final visit to the Riverside was for the 1-1 draw with Sheffield Wednesday this season.
Former England international Alan Peacock, pictured above with Rlando and Graeme Souness, played alongside him as his Boro career started and Rolando's came to an end.
"He was one of the nicest men I ever met in the game and this has come as a real shock to me," said Alan, chairman of the Middlesbrough Former Players Association.
"I played with him in my first few games and he seemed to like me. He really looked after me when I came into the side.
"Over the years he always kept in touch and I was planning to go and see him in the next few weeks.
"He was a real Middlesbrough fan and was always talking about the Boro. He was a great guy and a lot of people in the town knew him really well. He was a keen golfer and a man about town who loved to go to all the dances."
MFPA secretary Jim Platt added: "You couldn't wish to meet a nicer man than Rolando. I didn't meet him until we set up the Former Players Association, so I didn't see him play, but he used to come to a game every year. I was going to call him to invite him to the last game of the season.
"He was a true gentleman who was extremely popular with the fans and who loved football and loved coming to Middlesbrough."
After one visit to the Riverside, Rolando told mfc.co.uk: "When I come back to Middlesbrough it's fantastic, it's my second home and they treat me so well you feel as though you don't deserve it."