November 1993: The first Ultimate Fighting Championship (UFC) event is held in Denver, Colorado. Royce Gracie, a Brazilian jiu jitsu expert, wins the eight-man tournament, earning US$50,000 (S$69,000).
July 1997: padded gloves are enforced, and two weight classes - heavyweight (91kg and above) and lightweight (under 91kg) - are formed.
December 1997: UFC holds his first event outside the United States, staging UFC Ultimate Japan in Tokyo. July 1999: UFC adopts the 10-point scoring system from professional boxing.
January 2001: UFC is purchased by Zuffa LLC for US$2 million. Dana White is installed president, a position he still holds today. July 2002: UFC holds its first event in Europe, staging UFC 38 in London.
January 2005: UFC launches reality show The Ultimate Fighter, which proves a hit and helps turn the company's fortunes around.
December 2006: UFC acquires MMA organisation World Extreme Cagefighting for an undisclosed sum, and after running it as a separate entity for four years, absorbs the promotion in 2010.
December 2006: UFC 66 becomes the first UFC event - and first non-boxing event in North America - to cross one million pay-per-view (PPV) buys (1,050,000).
March 2007: UFC acquires popular Japanese MMA organisation Pride for a reported US$65 million. It also signs professional wrestling star Brock Lesnar.
July 2009: UFC 100, headlined by Lesnar and Frank Mir, becomes the first UFC event to cross 1.5 million PPV buys (1,600,000).
March 2011: UFC acquires MMA organisation Strikeforce for a reported US$40 million.
August 2011: UFC signs a seven-year broadcast deal with Fox Sports worth US$700 million.
December 2012: UFC launches a women's division and Ronda Rousey, Strikeforce's women's bantamweight champion, becomes the UFC's first female champion.
January 2014: UFC stages its first event in Singapore at Marina Bay Sands.
July 2016: Zuffa LLC, UFC's parent company, is sold to a consortium of investors led by WME-IMG for US$4.025 billion.
June 2017: UFC returns to Singapore. May 2018: UFC signs a five-year broadcast deal with ESPN worth US$1.5 billion. It starts next year.
June 2018: UFC announces a strategic partnership with the Singapore Sports Hub and the Singapore Tourism Board. It is the first multi-year live event deal for the outfit in the Asia-Pacific region and will see it stage shows at the Singapore Indoor Stadium till 2020.
October 2018: UFC 229 smashes PPV buy records by garnering 2,400,000 buys. Its biggest name, superstar Conor McGregor, earns a guaranteed cheque of US$3 million, before bonuses. The record PPV buys means he could eventually take home way more than that.
November 2018: UFC stages its 456th show, in Denver, to mark its 25th anniversary.