Under his leadership, the Victorian coalition shed 11 lower house seats in the 2018 "Danslide", including nine to Labor.
His party campaigned hard on law and order and Melbourne's so-called "African gangs" issue but Liberal elder Tony Nutt's election post mortem found voters saw it as a political tactic.
Specifically, the review said Mr Guy's infamous dinner with alleged mafia boss Tony Madafferi - immortalised with the "lobster with a mobster" headline - caused enormous damage to him and the opposition.
By election day, Mr Guy and his team were still a largely unknown quantity for too many.
The Bulleen MP had already resigned as leader when the review was published in November 2019.
With successor Michael O'Brien struggling to land a blow on the Andrews government's pandemic management, Mr Guy returned as leader in September 2021.
Within weeks, shadow attorney-general and factional ally Tim Smith drunkenly ploughed his Jaguar into the fence of a Hawthorn home.
He resigned from the opposition front bench but tried to ride out the scandal, initially defying Mr Guy's public call not to recontest his seat, before falling on his sword days later.
It was a friendship ender.
Successive Omicron waves in the new year further blew out Victoria's elective surgery waiting list, triple-zero call delays and ambulance response times.
The worsening health crisis allowed Mr Guy to stitch together a more compelling narrative compared to 2018 and soften his image, Monash University political scientist Zareh Ghazarian said.
"It's a really difficult job to be opposition leader," he told AAP.
"His media performances, as an observer, certainly have been consistently energetic and enthusiastic. It's very different in terms of tone and focus compared to 2018 and it had to be because the 2018 result was very poor."
The coalition's focus on health was redoubled after the Morrison government's federal election loss in May but Mr Guy's integrity was again called into question.
His chief of staff Mitch Catlin resigned after it emerged he solicited more than $100,000 in payments from a billionaire donor and sent the contract to the state Liberal leader's personal email address.
On the defensive for days, Mr Guy repeatedly declared nothing was agreed to or signed before handing documents to the Victorian Electoral Commission as part of a yet-to-be-completed probe.
Rebranding as "Matt Guy" on social media and official media releases, he vowed to shelve Labor's Suburban Rail Loop to redirect funds to the health system in a nod to Daniel Andrews' 2014 election strategy as opposition leader.
But more internal fissures have bubbled to the surface in the lead up to the November 26 poll, including the resignation of the party's in-house lawyer.
Based on published opinion polls, Mr Guy's coalition are poised for another four years in opposition.
Former Labor strategist turned RedBridge director Kos Samaras believes snaring 18 seats to govern in majority is a mountain too high.
His colleague and former Liberal deputy state director Tony Barry is slightly more upbeat, citing a poll from late last month that indicated more than a quarter of voters were uncommitted.
"It's going to be very difficult but it's so volatile and febrile out there you wouldn't rule it out," he said.
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