The 38-year-old will cycle with triathlete Phil Gray from Lisbon, in Portugal, to Newcastle via Porto, on Portugal's north coast, Eindhoven, in the Netherlands, Ipswich and London (Fulham and Wembley), visiting each of the grounds of teams managed by Sir Bobby.
Cycling around 150 miles a day, the journey is expected to take four weeks.
Robbie, who was described by Sir Bobby as Newcastle United's "very own Roberto Carlos", decided to take up the fundraising challenge after losing his father to cancer when he was just 16-years-old.
Robbie said: "It was really tough at the time.
"It's something you would wish on no one.
"If we can just raise the awareness and raise a bit of money towards helping out then we’ve done our job."
Phil added: "Obviously we're doing it for these two fantastic causes.
"It’s thinking about that and remembering that when we’re out on the ride that's really going to help us get through it."
Sir Bobby managed eight teams during his managerial career, starting at Fulham before moving on to Ipswich Town, England, Sporting CP, Porto, Barcelona, PSV Eindhoven and Newcastle United.
To donate text TREF03 and the amount you wish to donate to 70070, e.g. TREF03 £10.
Alternatively you can donate online here.
Following Robbie and phil each step of the way are filmmakers from Fantom Line, who will be making a documentary about the journey.
To find out more, visit bikeforbobbyfilm.co.uk
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