Here are the results of the Grasmere Guides race for Tommy Taylor:
1897 4th
1898 1st
1899 1st
1901 Taylor was indisposed (bout of flu)
1902 Taylor did not compete
The "Italian" would have been the local Guides runner and former champion Tom Conchie from Shap(winner in 1894, 1895, 1896 and 1897). He set the best time for the original course up Silverhowe of 14 min, 26 sec. in 1896.
Source:
Grasmere Sports. The First 150 Years.
The book "See the Conquering Hero Comes" says that "..in the absense of the champion hill climber, Tommy Taylor (Skelwith) who is a present in South Africa..." for the 1900 event.
Another early book is "Some Records of the Annual Grasmere Sports" published in 1911.
The course was changed in 1904 from Silverhowe to Butter Crags.
Copies of these books are available
here.