Team-mates shared the anguish in 1999 and 2000, while it also happened in 2005 and 2006.
It has happened twice more since, with Jamie Whincup and Scott McLaughlin suffering heartbreaks in 2010 and 2017.
As the countdown to the 2021 Repco Supercars Championship continues, Supercars.com has listed the six instances drivers have won the most races in a season, but failed to clinch the championship.
1999: Skaife's dozen not enough
Most wins: Mark Skaife (12 wins)
Champion: Craig Lowndes (9 wins)
Holden Racing Team heavyweight Mark Skaife won a staggering 12 races in 1999, but the title went to the other side of the garage.
Craig Lowndes claimed nine wins of his own, but missed an entire round following injuries sustained in his horrifying Calder Park crash.
Skaife's six round wins shadowed every other driver's haul, but Lowndes had already amassed a large lead by the time the series arrived Calder Park.
Lowndes clinched the championship by finishing second in the final round of the season at Bathurst.
2000: Lowndes loses out
Most wins: Craig Lowndes (10 wins)
Champion: Mark Skaife (7 wins)
Skaife hunts Lowndes in 2000 Pic: AN1 Images
The tables turned 12 months later, with Skaife besting Lowndes in what proved to be their final year as HRT team-mates.
Lowndes won 10 races to Skaife's seven, but Skaife won four rounds to Lowndes' three. However, they did share the Queensland 500 win.
Skaife sealed the championship with sixth place alongside Lowndes in the Bathurst finale.
2005: Bridesmaid Ingall pips Lowndes
Most wins: Craig Lowndes (6 wins)
Champion: Russell Ingall (2 wins)
Just two wins for Ingall in 2005
In 2005, Russell Ingall put years of heartache behind him to finally win the title.
A four-time series runner-up, Ingall claimed the championship ahead of Craig Lowndes, whose first Triple Eight campaign featured a season-high six wins.
Stone Brothers Racing team-mate Marcos Ambrose led the championship to the Bathurst 1000, but after his infamous accident with Greg Murphy, Ingall took over at the top.
Six drivers were in contention heading into the Phillip Island finale, and Ingall sealed the crown with fifth.
The then-41-year-old veteran helped SBR to a third straight championship, having taken just two race wins; Race 3 in Perth, and Race 2 at Oran Park.
Having finished runner-up in 1998, 1999, 2001 and 2004, an elated Ingall summed up his relief perfectly: "By about the 48th Jim Beam tonight, it will be sinking in quite nice."
2006: One and done for Mr Consistent
Most wins: Garth Tander (7 wins)
Champion: Rick Kelly (1 win)
Rick Kelly's 2006 title triumph saw the Toll HSV Dealer Team young gun claim just one race win.
It came on the streets of the Gold Coast after points were adjusted, with drivers required to drop the points from their worst round up to and including Bathurst.
Kelly's team-mate Garth Tander won seven races and two rounds, with title combatant Craig Lowndes winning five races and four rounds. Jason Bright and Todd Kelly also won five races each.
Despite not winning a single round or scoring a pole position, Kelly entered the Phillip Island finale seven points ahead of Lowndes. The duo were on equal points in the final race, but a collision between the two saw Lowndes come off worse and was forced to drag his car to 29th.
Kelly was penalised and finished 18th, which was enough to clinch his only championship.
2010: Whincup's 'what if' season
Most wins: Jamie Whincup (9 wins)
Champion: James Courtney (5 wins)
Jamie Whincup entered the 2010 season as a consecutive two-time champion, and kicked off Triple Eight's new era with Holden with six of the first eight race wins of the year.
After four rounds, he held a whopping 204-point lead over James Courtney. However, a hideous run of form across the next two rounds, compounded by four straight wins for Courtney, saw the lead swap hands.
He won three more races, at Darwin, Townsville and Surfers Paradise, to trail Courtney by just 53 points heading to the Sydney Olympic Park finale.
However, a rain deluge on Saturday forced the race leaders into the wall, all but famously handing the title to Courtney.
Whincup had nine wins to Courtney's five, but the title had slipped from his and Triple Eight's grasp.
2017: McLaughlin's heartbreaker
Most wins: Scott McLaughlin (7 wins)
Champion: Jamie Whincup (4 wins)
Scott McLaughlin was a force for DJR Team Penske, winning three drivers' titles on the trot between 2018 and 2020.
However, it could so easily have been four, had he sealed the deal in 2017.
He took a record 16 poles and won eight races, but a final day disaster in Newcastle saw Jamie Whincup run away with an unprecedented seventh championship.