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  1. Looks like a very late ’60s or early ’70s Grand Prix or Super Course, with a Shimano groupset added in the late ’70s or ’80s. The [1970 catalog](https://www.kurtkaminer.com/TH_raleigh_cat_70.html) looks identical, even having the same crankset. Red was one of the color options for the Grand Prix so I’d lean towards that model, but keep in mind that options varied by year and catalogs aren’t always correct. You might be able to find known examples of each bike and compare details. What size is the seatpost? 25.4mm would indicate high tensile steel tubing (Grand Prix) and 26.0mm would indicate straight-gauge Reynolds 531 (Super Course).

  2. I believe it’s a 1960s Raleigh Grand Prix. That head badge was used from about 1962 to 1970, from what I’ve read. The wrap over seat stay eyes was a feature of the Grand Prix. If you can find the serial number on the bottom bracket or left rear dropout, I think you could pin down the year. This bike likely came with Simplex Prestige delrin (plastic) shifters and derailleurs which deteriorated with UV exposure. They were likely replaced. This falls into the better range of their line, but there were about 5 bikes in their line that were better. Check the seatpost diameter. 25.4 is 2030 steel, larger seatpost diameter equals thinner, lighter tubing.

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