The men, aged between 61 and 77. are accused of physically and sexually abusing boys at the former St Ninian's School in Falkland.
All five pleaded not guilty to the charges at the High Court in Glasgow.
The accused are John Farrell, 72, Paul Kelly, 62, Edward Egan, 77, Michael Murphy, 75, and William Don, 61.
The 23-page indictment lists 131 charges involving more than 40 alleged victims.
The Roman Catholic school was run by the Christian Brothers organisation until St Ninian's closed in the 1980s.
Prosecutors allege a number of sexual attacks took place against pupils there.
Among others claims is an accusation that Mr Kelly left a young boy rolled up in a rug overnight.
He is also said to have hung another pupil upside down from a bridge.
Mr Farrell faces a charge that in the early 1980s he indecently assaulted a boy at a monastery on the isle of Iona.
He is further said to have attacked the same boy at a Catholic church in Motherwell in 1999.
Judge Lord Turnbull adjourned the case until a further hearing in July and no trial was set.
The attendance of Mr Egan and Mr Murphy will be excused at the next hearing.
Five men have appeared in court facing allegations of abusing pupils at a school that was run by the Christian Brothers in Fife between 1970 and 1983.