2000 – Pittance made history when he won three Listed Eye Liner Stakes in 2000, 2001 and 2002.
2001 – Mr W. Patch has held the position of the Ipswich Turf Club Chairman since 2001.
2001- Sydney Cup winner Henderson Bay also claimed the Ipswich Cup.
2004 – Portland Singa claimed the Ipswich Cup plus the Caloundra Cup and Group 1 Brisbane Cup in the same year.
2006 – Sphenophyta claimed the Ipswich Cup, he also added the Group 1 Turnball Stakes to his record later that year.
2007 – Ipswich Cup winner Sculptor was trained by Peter McKenzie who was also known for his role as Elendil in The Lord of the Rings: The Fellowship of the Ring. Sculptor went on to win the SAAB Quality at Flemington after his Ipswich victory.
2008 – Race caller Wayne Wilson picked the first seven winners of the 8-card meeting on a March meeting in 2008. Wayne was held in high regard in a career spanning 40 years with his first Ipswich call in 1969.
September 10, 2009 – The final three races at the Ipswich meeting were called off after jockeys went on strike at protest at changes to whip riding rules.
2009 – Our Lukas was the first horse to win back-to-back Ipswich Cup titles. His first was in 2009, followed by 2010 both for renowned Brisbane trainer Robert Heathcote.
2009 – Brent Evans was the first apprentice to win an Eye Liner Stakes. He won aboard Mitanni who was trained by John Wallace. Brent was also named the Apprentice School Champion for the same year. Brent was also the first apprentice to win a senior premiership in the same year.