But instead of an easy win, jaded voters caned Kennett. Particularly outside Melbourne, and with a young, new, last-minute leader in personable Steve Bracks (sound familiar?), Labor brilliantly exploited the Kennett Government having gone too hard for too long.
Chastened Liberals lost their majority and who governed was decided by three independents, two of whom had history with Kennett, just as Winston Peters had with English.
It took a month, but the independents chose Labor and Bracks became premier. Unexpectedly in Opposition, Kennett resigned but after years of his dominance the party had no obvious successor. A mild-mannered country vet, Denis Napthine, emerged but his was a temperament for government, not rough-and-tumble opposition.
From the outset, too, Napthine was stalked by his defeated leadership rival, Robert Doyle.
As well as lacking strong leadership, Victorian Liberals did not accept the 1999 result. They were convinced it was just a protest vote gone wrong, that an unprepared Labor government with an untried premier would sink, and the electorate's mistake would be corrected at the next election.
It wasn't. Bracks and the Labor leader he deposed, treasurer John Brumby, essentially kept Kennett's policy settings, but loosened purse-strings and gave those settings a more human face.
Bracks himself was young, likeable and competent, and his popularity rose as the electorate got to know him and his family. Instead of the expected brief spell in the paddock opposing a weak accidental government, the Liberals' denial turned to worry and then panic as the next election approached.
Shortly before that election in 2002, Napthine was rolled by Doyle and the divided Liberals blundered into one of the worst-run election campaigns in Australian history. As a result, Bracks won a landslide and, bar a one-term interlude, Labor has dominated Victoria ever since.
In making their own leadership decision, National MPs should Google this story and learn from it. Like the Victorian Liberals, National remains the largest party after last September's election, its policy and economic record under Key and English is widely respected, and its support in opinion polls is holding up.
As in Victoria, the election result effectively was decided by cross-benchers with a score to settle against the incumbents, with Peters installing a young, untried Prime Minister in Jacinda Ardern over English.
As has Ardern, in Victoria Bracks came to office with an inexperienced ministry seasoned by some old hands from the previous Labor Government. Faced, however, by a complacent Opposition failing to use the opportunity to refresh itself, and with the electorate both liking what they so unexpectedly saw and wanting to give the new Government a fair go, Labor successfully consolidated its position, read the politics far better than its complacent opponents, and stormed to re-election three years later.
National was cast into the wilderness by the capricious Peters rather than voters, and the slight softening of its support in the latest Colmar Brunton poll may have more to do with Ardern's pregnancy and a natural new government honeymoon. But if there is a conviction in the National caucus room that in 2020 Peters may be gone, Ardern struggling, and their own electoral support as strong as now, they're dreaming.
Whoever of the five candidates they choose – and the lack of a clear front-runner with a mandate itself is troubling – National MPs simply can't assume a one-term spell in the paddock, nor that Ardern's rickety Labour-led coalition will collapse.
That's not to say these things can't or won't happen, but any first-term Opposition must be prepared for the long haul. Whoever wins the leadership tomorrow, and despite the very good shape of the party bequeathed by outgoing leader English, uncertain times and renewal lie ahead for National regardless.
If the new National leadership doesn't accept and embrace that uncertainty, and use this term to build on the positives of the Key-English years while overhauling and renewing its team and programme, what happened to the Liberals in Victoria almost twenty years ago could yet happen to them.
• Terry Barnes is an Australian political commentator and columnist for The Spectator Australia magazine