The tunnel takes its name from the fact it passes through an area known locally as Robin Hood Hill.
The line was formally opened on 1 July 1850.
On the morning of Monday 22 November 1869, a passenger train collided with a goods train. The Huddersfield Chronicle reported that trucks would usually accumulate at Huddersfield Station over a weekend and then be shunted to sidings on the Penistone Line early on Monday morning. On this particular morning, damp weather led to the rails being "greasy" and the goods train came to a halt in the tunnel. The guard then placed explosive fog signals on the line to alert any approaching trains of the danger.
The 6:35am departure from Huddersfield to Penistone began braking after the driver heard the fog signal detonate but was unable to stop in time and the engine ran into the rear of the goods train. Several wagons were damaged and a number of passengers received injuries, some of whom took legal action against the Lancashire & Yorkshire Railway Company. Metal dealer William Brown, described as being an elderly man, was awarded £550 having lost the sight in one eye and been partially paralysed. Sarah Jane Taylor was awarded £175. Sheffield cutlery dealer Alfred Taylor (Sarah Jane's husband) was awarded £150 (after initially claiming for £1,000).