worst and best windows version

The Worst And Best Windows Version: An Ultimate Guide

All of Windows compared in one guide

Author: Jake, Marketing  
Last updated: March 26, 2018

In many ways, the history of Microsoft Windows is the history of the personal computer market.

The operating system [OS] has developed dramatically in functionality and security since Windows 1.0, a graphical user interface for MS-DOS, was launched in 1985.

However, if you have been using the OS through its lifetime you will know that there have been highs and lows. With this in mind, we've collated the worst and best Windows versions in one convenient list.

All versions of Windows 

  • Windows 1 [1985]
  • Windows 2 [1987]
  • Windows 3 [1990]
  • Windows 3.1 [1992]
  • Windows 95 [1995]
  • Windows 98 [1998]
  • Windows 2000 [1999]
  • Windows ME [2000]
  • Windows XP [2001]
  • Windows Vista [2006]
  • Windows 7 [2009]
  • Windows 8 [2012]
  • Windows 8.1 [2013]
  • Windows 10 [2015 -]

Moving beyond just a productivity tool, the recent, and arguably best Windows versions have become a base to a modern cloud workspace. You’ll be able to see what this means below.

In addition, you can also check out some of the common questions around Windows.

windows roadmap guide

A history of the worst and best Windows versions

Windows has, with the passing of the years, introduced more and more new features to further bolster its usefulness to the enterprise.

For example, Windows 2.0, released in 1987, allowed Windows to overlap each other for easier multitasking, while 1992’s Windows 3.1 brought Truetype font support, making the operating system more suitable for office work. Later enhancements included the tablet-friendly features introduced with Windows 8 in 2012.

With all of these difference features, we’ve compiled them into one collection that contains all Windows versions, for those who are visual, here is a in-depth infographic:

Best Windows Versions Infographic

P.S. If you feel that this would be valuable to your community, hit one of the share buttons on the left.

Now that you have got a high level, let’s get into rating them [feel free to disagree in the comments section below].

Scoring for the best Windows versions

Windows 1 [1985]

Best feature

Graphical user interface means it was easy for home computers. Allowed developers to easily design applications for Windows.


Demanding hardware, dependant on mouse-orientated interface, lack of dedicate software, poor performance.

Rating: 8/10

Windows 2 [1987]

Best feature

Allowed more than one application to run at once. Introduced short-cuts. Introduce ‘minimize and maximize’. Introduced desktop icons. Faster and much more powerful.


Still very dependant on the DOS system and still hadn't passed the 1 megabyte mark in terms of memory.

Rating: 6/10

Windows 3 [1990]

Best feature

Allowed more than one application to run at once. Introduced short-cuts. Introduce ‘minimize and maximize’. Introduced desktop icons. Faster and much more powerful.


Limited for the home use market, where most games and entertainment programs continued to require raw DOS access.

Rating: 5/10

Windows 3.1 [1992]

Best feature

Allowed more than one application to run at once. Introduced short-cuts. Introduce ‘minimize and maximize’. Introduced desktop icons. Faster and much more powerful.


Limited for the home use market, where most games and entertainment programs continued to require raw DOS access.

Rating: 7/10

Windows 95 [1995]

Best feature

Introduced Internet Explorer. Introduced the ‘start-button’. ‘windows explorer’ replaced the start menu. Simplified ‘plug-and-play’ features.


Multi-tasking was glitchy. There was security issues with file and printer sharing. There are also security issues with varying applications; prone to viruses.

Rating: 5/10

Windows 98 [1998]

Best feature

Introduction of Outlook, Microsoft Chat, Windows Address Book, back and forward navigation buttons, image thumbnails, folders, famous ‘Windows Start-Up sound’.


Plug and Play had big issues. USB devices never worked properly. Virus software was hard to install which was an issue as 98 was prone to viruses.

Rating: 7/10

Windows 2000 [1999]

Best feature

Ability to launch multiple programs without closing the menu. It was incredibly stable. Were able to set profiles for different users who accessed a pc running the OS.


Requires high spec hardware so a lot of users had to upgrade their machines. Log-on authentication controlled file access meaning files could not be shared between accounts.

Rating: 9/10

Windows ME [2000]

Best feature

Made more simple to use for ‘home computer users’. Removed certain enterprise-orientated features which gave it faster loading/booting speeds.


Can’t handle more than 512 MB of RAM/ Dubbed ‘Windows Mistake Edition’. It was unstable and kept crashing.

Rating: 2/10

Windows XP [2001]

Best feature

Included additional multimedia features such as ability to record, watch DVD’s and listen to music. Extremely user friendly and stable.


It was expensive to buy. It was a prime target for malware creators and the security was bad. It could only support up to 4GB of system memory, meaning you couldn't run applications that require a lot of system memory.

Rating: 6/10

Windows Vista [2006]


It was very secure, including: parental controls, encryption features and has an advanced firewall. It had enhanced video quality and photo gallery. It had a task bar and thumbnails.


It needed a demanding computer to run with high memory. Doesn’t really work on anything less than 2GB of RAM. High graphics card requirement. Visually a bit too dull.

Rating: 7/10

Windows 7 [2009]


Designed for touch screen interaction. Very fast. Includes ‘Windows defender’ which is the very good protection system. Supports virtual hard disks. Customizable and easy to use.


It required high RAM to work. It was very expensive. Older software was incompatible with Windows 7.

Rating: 5/10

Windows 8 [2012]


It booted up really fast. Windows store has a number of apps that are built for Windows 8. Supports NFC: wireless printing/payment.


Very difficult to swap between screens as no alt-tab function. Doesn’t support any flash content on Tablet PC. Metro interface does not work well on desktop and it is not user friendly.

Rating: 7/10

Windows 8.1 [2013]


Fast boost mode enabling your PC to boot up in under 4 seconds. The start button makes a reappearance. Windows media centre offers a wider range of audio-visual file types. Improved firewall and security features.


Many pre-installed apps are not used at all and use up quite a lot of hard disk space. System requirements are quite high. The start screen works better with touch devices.

Rating: 8.5/10

Windows 10 [2015 -]


Cortana voice assistant integrated into the browser. Easy social media integration. Upgrade from Windows 7, 8.1 and Windows phone 8.1. Great for gaming thanks to Direct X 12 API. Introduction of Xbox app (see what your friends are doing online). Comes with two browsers: Spartan & Internet Explorer.

Rating: 10/10

So, which version is the best?

Of course it would be easy to say that the latest iteration of Windows is the ‘best’, but in reality, you tend to find that there is a version of great innovation, with large issues. This is then followed by minimal, but significant tweaks that enable the previous version to succeed.

As such, it’s difficult to know which of the two is more impactful.

Overall, one can say that with the ‘evergreen’ approach to Windows 10, and the huge levels of user adoption, it will undoubtedly mould itself to become the greatest version to current users.

Windows is a powerful three-pronged solution

In addition to the great value demonstrated from a productivity perspective, the value of Windows is far greater.

In reality, there are three comprehensive Windows-based solutions that have becoming incredibly appealing to businesses. These are as follows:

  • Windows 10
  • Windows Server 2016
  • Microsoft & Citrix VDI

Windows 10: a game-changer in enterprise security

While keeping an intuitive user experience, Windows 10 has brought major security enhancements over its predecessors.

It really is the best of all previous Windows versions.

For example, multi-factor authentication keeps information safe should the device be lost or stolen, while biometrics can be utilised for more secure login. Windows 10 also maintains a similar user experience across a wide range of devices, including desktop and mobile devices, thus removing tricky learning curves that could hamper your corporate operations.

Windows 10 also allows businesses to choose the rate at which they innovate - allowing organisation to become an example of digital transformation.

You can choose the rate that fits your needs and those of your customers. Functions including locking down business critical environments and keeping segmented user bases well-supplied with updates are possible, while you can even improve your IT management’s cost-efficiency.

The arrival of Windows Server 2016

In addition, you have the computational ability of Windows Server 2016, which is open to general availability.

This is “a cloud-ready OS” that “inherently enables hybrid cloud”, as declared by Microsoft.

The hybrid cloud that Microsoft enables with Windows Server 2016 can connect businesses across cloud environments, but also provide a consistent user experience where the resource’s location does not lead that experience to differ between IT professionals, developers and end users.

This consistency also allows businesses to draw upon the right cloud resources when they need them and developers to build applications and services that can be easily deployed in different locations based on corporate rules and technical needs.

A promising new collaboration between Microsoft and Citrix

In August, Microsoft revealed that it would “gradually wind down the delivery of Azure RemoteApp”.

We had previously described RemoteApp as a modern alternative to traditional VDI” (Virtual Desktop Infrastructures).

However, while many businesses had opted for Azure VDI, solutions in this area could be expensive to use correctly. Therefore, it was not always convenient to consume high-quality media and collaboration content from a VDI deployment in particular.

See a great video here that explains its advantages:

Microsoft has announced that it is partnering with Citrix to develop an alternative service to RemoteApp – and we have suggested that it might give us the best of both worlds”.

What worlds?

It could enable businesses to both access their desktops from anywhere and, on other occasions, take their desktops with them to ensure that they can reach their data and apps from anywhere.

Windows FAQs

In addition to the information about surround the OS, best Windows versions and more, here are some common questions:

1. Who Invented Windows?

Bill Gates and Paul Allen invented Microsoft Windows in 1983, and Windows 1.0 was ready for use by 1985. It was named “Windows” because the user was able to change between screens, similar to how would look out a different window. Source

2. What Year Was Windows Released?

November 20, 1985

3. Why is Windows Called Windows?

In early 1980s Microsoft works on the first version of a new operating system. Interface Manager is the code name and is considered as the final name, but Windows prevails because it best describes the boxes or computing “windows” that are fundamental to the new system. Source

4. When Did Windows Come to MAC?

Bootcamp is most commonly used to run windows on MAC. The first version launched in 2006 which was after the release of Windows XP.

5. How Many Versions of Windows Are There?


6. How Many Computers Run Windows?

In 2011 1.25 billion computers were running windows. Today Microsoft accounts for 91% OS share of all computers worldwide.


Well, that’s our summary, make sure to let us know your thoughts on the best Windows versions, and the various enterprise elements of Windows.

windows roadmap guide

Topics: Infographic, Workspace, Windows

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