The key events in the motorsport career of Jamie Whincup outlined ahead of his retirement from full-time driving later this year.
| 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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