The Pakenham Cup used to be run in early December each year. It took over the Listed status from the Werribee Cup in 2016, the year the Pakenham Racing Club began racing at its new track at Tynong. In 2016 Pilot D’Essai carried 58kg after winning the Ballarat Cup at his previous outing.  In the following three years Like A Carousel, Our Big Mike and Etah James all won with 54kg, then in 2020 Attorney lumped 59.5kg to victory.

In 2022 it was held on 3rd December then the timing was changed from December to a night meeting in early March which means it was not run in 2023. The change was decided on after the recently-merged Pakenham Racing Club and Cranbourne Turf Club moved to increase its autumn footprint.

In 2024 it was moved back to December, meaning it was run twice that year.

2024 Pakenham Cup Preview and results. (March)

2022 Pakenham Cup Preview and results.

2021 Pakenham Cup Preview and results.

2020 Pakenham Cup Preview and Results.

Last mare to win: Etah James (2019)

Multiple winners: Magistrate (1980 & 1981)

Fastest time (2500m): Our Big Mike (2018) 2:34:68

Interesting trivia: His 2022 win on Kissinger gave jockey Damien Oliver his 4th Pakenham Cup.

Winners of past Pakenham Cups include Etah James (2019), Like A Carousel (2017), Roman Arch (2005), Makybe Diva (2002), Slavonic (2000), Ideal Centreman (1989), Fountaincourt (1983), Even Stevens (1962), Sir William (1956).