In 2005, Pickens competed at the Chili Bowl midget car race at Tulsa, Oklahoma. He won Rookie of the Year honors with an outstanding drive from 19th starting position to a race ending 6th-place finish. He was noticed by some key people at NASCAR NEXTEL Cup's Roush Racing. While not having prior experience on pavement, as there are no pavement ovals in New Zealand, Pickens did compete in the Roush's Driver Development Competition Program in 2005. He made it to the final round of competition and was the last driver be cut.
In 2005, Pickens won the 55th running of the Australian Speedcar Grand Prix held at the Avalon Raceway in Victoria. That year he also finished second in the Australian Speedcar Championship at the Perth Motorplex. He would later finish 3rd in the 2011 Australian Championship in Lismore, New South Wales. In 2016 Michael won the Australian Speedcar title at Paramatta Raceway.
Michael's regular rides in New Zealand are Brett and Leigh Morris' Seamount #1AU Midget and the Pipeline Industries #54 Sprint car. Michael's regular Australian drive is with Brett Morris, competing in the Australian Speedcar Championship and the World Midget Series. Michael's regular USA drive is with Jerome Rodela, competing in the Turkey Night Grand Prix and Chili Bowl Nationals.
In the middle of the 2007 U.S. season, he raced for Ken Hendricks’ American Speed Association Late Model Team, Urban Force Racing, mainly at Madison International Speedway. He left the team in July (being replaced by Dan Lensing) near the middle of the season, and began running a mixture of midget and pavement car races for various owners.
In the 2008 U.S. racing season, he raced a midget car weekly at Angell Park Speedway and the #30 car in ASA Late Model Series events.
2016 Australian Speedcar Champion (and first ever New Zealander to win this title)
2015/16 International Midget Series Overall Winner (and winner of World 30 Lap Derby and 50 Lap Classic)
7 times New Zealand Midget Champion
Multiple winged sprint car feature wins
Multiple track and lap records
Multiple National Series Championship wins
Multiple A-main wins including 9 consecutive A-main wins in a row
4 times New Zealand midget Grand Prix win
2 times North Island champion
5 times Barry Butterworth 40 lap winner
Multiple International Series wins over 30, 40 and 50 laps
Multiple seasons as International Test Team Captain
Multiple Herman Tros shield wins
Multiple USAC/POWRi/Badger feature wins
6 times Chili Bowl A-main qualifier
3rd 2011 Chili Bowl A-main
UMRA TQ feature winner (on debut)
2 times Australian Super Series speedcar Championship winner (midgets)
Australian Grand Prix winner (midgets)
ASA Pavement Late Model Series feature and pole winner
NASCAR Craftsman Truck Driver X finalist