Stood on the North East corner of Fleet Street and South East corner of Bedford Street.
First recorded in the 1849 directory, J. Deacon its’ licensee. Followed by James Walker in 1864, William Iveson in 1871.
When Steven Walker became the owner, the following licensees completed the list for the Woodboy: 1876, Charles Bodycott. 1885, Edward Malpas. 1889, Thomas Baylis. 1894, James Burke. 1899, James Pratt. During this year Leicester Brewing & Malting became the new owners.
In 1903, James Halford became licensee followed after his death by Edward Halford. 1914 saw Benjamin Vaughn who, after he died, was followed by Julia Vaughn.
A renewal of the licence was objected to in 1920 and referred to the Compensation Act. On 30 March 1922 the tenant was paid £170 with the Brewery receiving £1687. The Woodboy finally closed on the 6th of April 1922.