| 2000 |
Formula Ford debut |
| 2002 |
Supercars debut, with Garry Rogers Motorsport in enduros |
| 2002 |
Wins Australian Formula Ford championship |
| 2003 |
Rookie Supercars Championship season, with GRM; loses drive at end of year |
| 2004 |
Enduros only, with Perkins Engineering; finishes ninth in Bathurst 1000 with Alex Davison |
| 2005 |
Back in full-time seat with Tasman Motorsport; finishes third in Sandown 500 then second in Bathurst 1000 with Jason Richards |
| 2006 |
Wins first race for Triple Eight Race Engineering, in Adelaide |
| 2006 |
First Bathurst 1000 win, with Craig Lowndes; final (effective) lead change is his pass of Todd Kelly upon the Lap 110 restart |
| 2007 |
First Supercars pole, at Queensland Raceway |
| 2007 |
First Sandown 500 win |
| 2007 |
Wins Bathurst 1000 with Lowndes |
| 2008 |
Record-equalling third consecutive Bathurst 1000 win, still with Lowndes |
| 2008 |
Spins into ditch during cool down lap television interview after race win at Symmons Plains |
| 2008 |
First Supercars Championship win |
| 2009 |
Wins Supercars Championship |
| 2010 |
Leads Lowndes to one-two in Triple Eight’s very first race in Holdens, at Yas Marina |
| 2010 |
Finishes second in Triple Eight one-two at Bathurst 1000 |
| 2010 |
Finishes second in championship after all three contenders go into the wall simultaneously in a penultimate day thunderstorm at Sydney Olympic Park |
| 2011 |
Wins Supercars Championship |
| 2012 |
Wins Bathurst 1000 with childhood friend Paul Dumbrell after withstanding late pressure from David Reynolds |
| 2012 |
Wins Supercars Championship; unofficially sealed title with event to spare |
| 2013 |
First Bathurst 1000 pole |
| 2013 |
Makes audacious attempt to snatch lead on final lap of Bathurst 1000 at Griffins Bend but has to settle for second |
| 2013 |
Wins Supercars Championship despite a number of nervous moments in final race at Sydney Olympic Park |
| 2014 |
Breaks Peter Brock’s pole record with his 58th, at Sydney Motorsport Park |
| 2014 |
Runs out of fuel while leading on final lap of Bathurst 1000 after defying team orders and finishes fifth; had started from second-last row after crashing in qualifying |
| 2014 |
Record fourth straight Supercars Championship win; unofficially sealed with one event to spare |
| 2015 |
Penalised for passing Safety Car after defying team orders to pit in the latter stages of the Bathurst 1000 |
| 2016 |
100th Supercars race win, at Sydney Motorsport Park |
| 2016 |
First to chequered flag but does not win Bathurst 1000 due to penalty for clash with Scott McLaughlin which leads to latter’s S60 and Garth Tander’s Commodore being wiped out |
| 2016 |
Triple Eight’s appeal against that penalty dismissed; Whincup would state in a 2019 interview that he still considers sanction ‘brutal’ and wrong |
| 2017 |
Wins Bathurst 12 Hour with Lowndes and Toni Vilander in a Ferrari 488 GT3 |
| 2017 |
Passes Lowndes for greatest number of Supercars Championship race wins with his 106th, at Sydney Motorsport Park |
| 2017 |
Wins record-extending seventh Supercars Championship title in one of the most exhilarating and controversial finales ever, in Newcastle |
| 2018 |
Leads Triple Eight one-two-three in Sandown 500 |
| 2018 |
His car loses a wheel while holding second on Lap 40 of Bathurst 1000; finishes 10th despite being off the lead lap until Lap 94 |
| 2018 |
Buys 15 percent share in Triple Eight |
| 2019 |
Penalised at Pukekohe for passing an erroneously deployed Safety Car which would have likely cost him victory anyway; makes infamous ‘red wine’ quip shortly after the race |
| 2019 |
Briefly faces prospect of Bathurst 1000 ban but ultimately avoids that and a fine after issuing apology to officials |
| 2020 |
Pays tribute to Holden workers after winning Race 1 of season, following the announcement that the marque would be closed down just three days earlier |
| 2020 |
Qualifies on pole for what would have been 500th Supercars race, at Albert Park, but that is abandoned along with the rest of the Australian Grand Prix |
| 2020 |
122nd Supercars race win thus far, in Townsville |
| 2021 |
Announces retirement from full-time driving at end of the year |
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