27 moments · 1984 – 2025
41 years of the same argument.
HouseWhat happened is the scoreboard. What it meant is us, and that only ever appears in amber.
1984 – 1989
First blood
One company sells a computer with a mouse. The other sells a program that puts windows on the computers everybody already owns.
The Macintosh, and the ad that ran two days before it
Ridley Scott's “1984” aired during the Super Bowl on the 22nd and the Macintosh went on sale on the 24th at $2,495. It had a mouse, a bitmapped screen and a desktop metaphor almost nobody outside a research lab had ever used.
What it changed
Set the terms of every argument since: one company sells the whole machine, and charges for it.
HouseThe ad promised the computer would stop you becoming a conformist. It has been sold to conformists ever since, which is not the machine's fault.
Windows 1.0 ships, and it cannot overlap a window
Microsoft's answer was not a computer but a program you ran on top of MS-DOS. Version 1.0 tiled its windows rather than stacking them, ran on hardware you already owned, and was reviewed as underwhelming almost everywhere.
What it changed
Fixed the shape of the fight: one integrated machine against one piece of software that runs on everybody else's.
Apple sues Microsoft over the look and feel
Apple alleged that Windows 2.0 copied the Macintosh interface. Microsoft's defence leaned on a 1985 licensing agreement covering visual elements — one Apple had signed to keep Word and Excel coming to the Mac.
What it changed
The last serious attempt to settle this in a courtroom rather than a shop.
1990 – 1996
The Windows decade
Windows takes the desktop so completely that the interesting question becomes whether Apple survives the decade.
Windows 3.0 is the one that works
Better memory handling, a Program Manager people could understand, and an installed base of cheap PCs to land on. It sold in the millions and made Windows the default assumption of office computing.
What it changed
The desktop stopped being contested and started being Windows.
The lawsuit collapses
The courts found that most of what Apple claimed was either licensed under the 1985 agreement or not protectable at all — you cannot copyright the idea of a window. Apple's appeals ran out without changing the outcome.
What it changed
Interface conventions became common property, which is why both machines still feel broadly alike.
1997 – 2006
The comeback
Apple is kept alive by its rival, ships a new operating system and a new processor architecture, and starts running ads about you rather than about computers.
Apple buys NeXT and gets Steve Jobs back
Apple needed a modern operating system and had failed to build one twice. It bought NeXT for around $400 million, and with it the Unix foundation that became Mac OS X — and the founder it had pushed out in 1985.
What it changed
Every Mac since runs on software Apple had to buy from outside, after its own attempts failed.
Bill Gates on the screen at Macworld
Jobs announced a deal: Microsoft would take $150 million in non-voting Apple stock and commit to five more years of Office for Mac. Internet Explorer became the Mac's default browser. Gates appeared on a screen above the stage and the hall booed.
What it changed
The rival kept the fight alive. It is the most quoted fact in any Mac-versus-Windows argument, and usually the most garbled.
HouseIt was not a bailout — Apple had cash in the bank. It was the end of the lawsuits and a guarantee that the Mac would keep running Office, which mattered far more.
The iMac drops the floppy drive
Translucent blue, no floppy, USB only, one price. The press called the missing drive a mistake; the machine sold anyway and pulled USB onto every peripheral maker's roadmap.
What it changed
Established the pattern Apple has repeated ever since — remove the port, absorb the complaints, be right on a five-year horizon.
HouseIt is also the pattern behind every dongle you now own. Being right on a five-year horizon is cold comfort in year one.
Mac OS X puts Unix under the desktop
The NeXT foundation reached the public: protected memory, pre-emptive multitasking and a real command line under a new interface. Early releases were slow and short on software, and plenty of people kept booting back into OS 9 for a year or two.
What it changed
Gave the Mac the thing developers would later move to it for — a Unix shell on a laptop with good battery life.
Windows XP merges the two Windowses
XP put the consumer line and the NT line on one codebase, which is why it was stable enough that people refused to leave it for over a decade. Microsoft supported it until 2014 and had to campaign to get anyone to move.
What it changed
The high-water mark for Windows goodwill, and the ghost that two later releases were judged against.
Macs switch to Intel, and start running Windows
Apple moved the whole line from PowerPC to Intel inside a year. In April it shipped Boot Camp, which let any new Mac boot Windows natively — a feature it advertised rather than buried.
What it changed
For fourteen years one machine could be both, and switching stopped being a one-way door.
HouseThis was the most persuasive argument the Mac has ever had, and Apple gave it up in 2020 without blinking.
Get a Mac: two men in front of a white wall
Dozens of television spots between 2006 and 2009, each a short scene in which a relaxed young man is the Mac and a decent, doomed man in a suit is the PC. Microsoft answered in 2009 with Laptop Hunters, in which real people were given a budget and sent shopping.
What it changed
Turned the argument into a personality test rather than a spec comparison. It has never gone back.
HouseThis site exists because that framing worked. The ads were also unbearably smug, and the reply — which was simply about money — is the only Microsoft advertising anybody still quotes.
2007 – 2019
Stalemate
Both sides take turns shipping the version everyone skips. The fight moves from features to keyboards, ports and stands.
Windows Vista arrives and nobody wants it
Vista brought a security model that broke drivers, hardware requirements that machines sold as ready for it could not meet, and a permission prompt that fired constantly. Businesses skipped it. XP stayed.
What it changed
Handed Apple the best three years of advertising it ever had, at the exact moment it had an Intel Mac to sell.
Windows 7 fixes it
The same architecture as Vista with the compatibility repaired, the prompts calmed down and window snapping added. It promptly became the version people refused to upgrade from next.
What it changed
Restored Windows' reputation, and taught a generation of users to skip one release and take the next.
The MacBook Air at $999
The redesigned Air came in 11- and 13-inch sizes with flash storage, no optical drive and instant wake. Intel launched its Ultrabook specification the following year and put a $300 million fund behind getting PC makers to build something like it.
What it changed
Set the shape of the thin laptop for a decade, on both sides of the line.
The Retina MacBook Pro
Double the pixels in each direction, memory soldered to the board, and a battery glued into the case. iFixit gave it the worst repairability score it had handed a laptop at that point.
What it changed
The screen argument was over for years. So was opening your own laptop.
HouseBoth halves of that sentence are still true, and the second one is the entire case for the other side.
Windows 10, free, and pushed hard
A free upgrade for Windows 7 and 8 users, delivered by a prompt that grew steadily more insistent until closing it with the X was treated as consent. Microsoft apologised for that part. Adoption was fast.
What it changed
Windows became something that updates itself rather than something you buy in a box.
Four ports, a Touch Bar, and a dongle for your dongle
The MacBook Pro lost every port except USB-C, replaced the function row with a touchscreen strip, and shipped alongside an iPhone that still charged over Lightning. Apple cut adapter prices for a year in response to the reaction.
What it changed
Made “what do I have to buy to plug this in” a standard part of buying a Mac.
HouseThe Touch Bar was gone by 2021. The ports came back the same year. Rarely does a company mark its own homework this legibly.
The butterfly keyboard ends, four years late
The thinner key mechanism introduced in 2015 failed on dust, repeated characters and dropped others. Apple ran a free repair programme from 2018 and went back to a scissor mechanism with the 16-inch MacBook Pro in November 2019.
What it changed
Four model years of laptops whose defining flaw was the part you touch most.
HouseThe house keeps this entry because build quality is Apple's strongest card, and a card that good is worth holding honestly.
2020 – now
Silicon
Apple changes the chip and the battery argument ends. Microsoft answers with hardware requirements, an AI button and a deadline.
Apple silicon ends the battery argument
The M1 MacBook Air had no fan, ran Intel software through Rosetta 2 faster than some Intel Macs ran it natively, and lasted a working day on a charge. Boot Camp did not make the trip: an Apple silicon Mac cannot boot Windows.
What it changed
Performance per watt stopped being a talking point and became the reason people switched.
HouseThe strongest hand either side has been dealt since 1995 — and it cost the Mac the one feature that made switching risk-free.
Windows 11 draws a hardware line
The upgrade was free, but it required TPM 2.0, Secure Boot and a processor from Microsoft's supported list. Working PCs only a few years old were ruled out, and the workarounds came with a warning that updates were not guaranteed.
What it changed
For the first time in decades, a Windows upgrade was something your hardware could be refused.
The last Intel Mac is replaced
The Mac Pro moved to Apple silicon, closing a transition Apple had said would take two years. Every Mac on sale runs Apple's own chips, and macOS support for Intel models has been winding down since.
What it changed
The dual-boot decade ended for good. A virtual machine is the only Windows a new Mac will run.
Copilot+ PCs, an ARM answer, and Recall
Microsoft's Copilot+ machines shipped on Snapdragon X chips with a neural processor and a dedicated Copilot key, alongside Recall — a feature that took continuous screenshots to make your past searchable. Security researchers took it apart before launch and Microsoft pulled it back for rework.
What it changed
Windows got competitive battery life and a privacy argument on the same day.
macOS finally tiles windows
Sequoia added built-in snapping: drag a window to an edge, or use the keyboard, and it takes half the screen. Until then it took Rectangle or Magnet, and everybody who had ever used Windows mentioned it.
What it changed
Closed the most-cited gap in the daily experience of moving from Windows to a Mac.
HouseWindows has had this since 2009. Fifteen years is a long time to hold out on a feature you ship in the end anyway.
Windows 10 support ends
Security updates stopped on 14 October 2025 for a version still running on a very large share of the world's PCs, with a paid extended-updates programme as the alternative. Many of those machines cannot take Windows 11 under its own hardware rules.
What it changed
The largest forced hardware decision in desktop computing for years — and the best recruiting moment either side has had since Vista.
HouseEvery one of those owners is, briefly, a switcher. That is the real reason this site started counting rounds when it did.
HouseAnd that is where you came in.
Four decades, and the honest summary is that each side has spent most of them fixing the thing the other one got right first. Which is why this site scores rounds instead of declaring a winner — the lead changes hands roughly once a decade, and anyone who tells you otherwise has simply stopped checking.
Read the card as it standsOr the myths this history produced