Three men are facing a total of more than 300 charges involving "front-running", a form of insider trading.
Front-running involves a broker trading a stock in his personal account based on advance information that he possesses of pending orders to buy or sell shares of a company.
Leong Chee Wai, Toh Chew Leong and Simon E Seck Peng have been charged with offences allegedly committed between 2007 and 2014, said the Monetary Authority of Singapore (MAS).
They are alleged to have front-run 49 locally listed counters - including Ascendas Real Estate Investment Trust, CapitaMalls Asia and Global Logistic Properties, among others - as well as 51 foreign-listed counters.
This is the first front-running case to be prosecuted here.
Leong, 47, was working as a dealer in First State Investments Singapore (FSI) at the time of the alleged offences.
He had information about whether FSI intended to buy or sell these shares, the size of the orders, the price range of the orders and when they would be completed.
One case involved the trading of property firm Allgreen's shares. Between July 2007 and February 2008, he allegedly asked E, 47, to both buy and short-sell Allgreen shares using his personal trading account before FSI completed its intended orders.
From August 2008 to 2009, Leong allegedly conspired with Toh, 40, once again to get E to carry out trades on his personal account based on insider information. Leong is facing 115 charges under the Securities and Futures Act, while Toh is facing 111 and E, 107.
If convicted, Leong, Toh and E could each face fines of up to $250,000 or a jail term of up to seven years, or both.
This is the second securities fraud case jointly brought by the MAS and the Singapore Police Force's Commercial Affairs Department (CAD).
The first involved a former remisier, Malaysian Dennis Tey Thean Yang, 32, who was charged with lodging fake bids to create the appearance of interest in a stock.
In March last year, the MAS and the CAD had said that they would jointly investigate market misconduct such as insider trading, whereas previously the two agencies would conduct investigations independent of each other, depending on whether the targeted offence was likely to be a civil penalty or criminal prosecution case.