Martin Reagan, 88, is now living in a care home in Kirk Hammerton, York, and has recently been suffering from ill health.
However, when manager Tony Mowbray heard about his recent problems, he sent a signed shirt bearing Martin's name and Boro number and a message sending the club's best wishes.
Speedy outside-right Martin played 25 games and score four goals for Boro from 1948 to 1951 after joining the club from Hull City for £4,000.
He left for Shrewsbury Town for £2,500 in August 1951 and also had spells with hometown club York City, Portsmouth and Norwich City.
"Martin has fond memories of playing for Middlesbrough and receiving this shirt signed by Tony Mowbray really made his day special," said family friend Lee Elgie.
"It's good to know our club are there to support those who have worn the red shirt."
Our pictures show Colin Elgie, Martin, Oaklands care home manager Yvonne Dobson and Martin's sister.
Boro's oldest surviving player, just a couple of months older than Martin, is Stan Rickaby, who lives in Australia.
Boro's Oldest Surviving Players
1. Stan Rickaby (born March 12 1924)
2. Martin Reagan (born May 12 1924)
3. Rolando Ugolini (born June 4 1924)
4. Harry Bell (born October 14 1924)