John Holland and an employee were felling a tree at a house in Deeping St James, Lincolnshire, last August. They were both using a chainsaw, despite not being qualified to do so, and neither was wearing protective clothing or a harness when working on the crown.
The Health & Safety Executive (HSE) brought the prosecution at Spalding Magistrates' Court.
Holland, of Spalding, Lincolnshire, pleaded guilty to breaching Regulation 6(3) of the Work at Height Regulations 2005, Regulations 4(1) and 4(2) of the Personal Protective Equipment at Work Regulations 1992 and Regulation 9(1) of the Provision and Use of Work Equipment Regulations 1998.
Spalding magistrates this week fined him £4,000 and ordered him to pay costs of £2,000.
HSE inspector Neil Ward commented: "It is sheer good fortune that no-one was hurt that day."