NHS Fife was forced to shell out £180,000 on a single legal claim, as the health board’s total costs passed £1.8 million in five years.
The large claim was among 142 made by patients from 2018 to June 2023.
In 2018, the largest cost for a single claim was £183,145, while another in 2020 came in at just under £105,000.
Meanwhile, in Tayside the total figure spent on legal costs is significantly higher, with the bill totalling in excess £6.59 million.
In all, 345 claims were recorded against the health board, of which 176 were described as clinical complaints.
NHS Tayside also set out the top 10 categories of claims against it by disgruntled patients.
Asked about the claims, a spokeswoman said: “The data provided represents legal settlements and payments for a wide range of claims.”
Clinical issues such as delayed diagnosis topped the list, with slips and falls due to debris or an uneven surface coming in second.
Other issues prompting claims include needlestick injures, medication errors and confidentiality breaches.
NHS Fife said it could not detail the categories of each claim as the small numbers could identify those involved.
Across Scotland, £61 million was spent on legal costs.
Scottish Conservative health spokesman Dr Sandesh Gulhane MSP said: “My heart goes out to the patients and families who have suffered as a result of failings in Scotland’s NHS.
‘Buck stops with SNP’
“But the buck for this stops with a succession of SNP health secretaries – including Humza Yousaf and discredited Michael Matheson.
“These figures are a damning indictment of their dire workforce planning, which has left our health service woefully under-resourced.”
Dr Gulhane, an NHS GP, said staff were “dangerously overstretched”, which would lead to more mistakes.
In October The Courier revealed how one Fife paramedic said burnt out staff feared making a deadly mistake.
Dr Gulhane added: “Scotland’s NHS is lurching from crisis to crisis under SNP mismanagement – and Humza Yousaf’s flimsy recovery plan has failed to remobilise it.
“Ministers must match the Scottish Conservative plans for a modern, efficient and local health service.”