OpenAI ChatGPT vs Microsoft Microsoft 365 Copilot
Founder, Automation Squad
A spec-by-spec, SquadScore™-driven breakdown of these two ai assistants & chat. Every metric is normalised and weighted so the winner is decided by the data.
The verdict
Winner: OpenAI ChatGPT — SquadScore 77.1 vs 64.8.
The OpenAI ChatGPT takes this matchup with a SquadScore of 77.1, a 12.3-point margin over the Microsoft Microsoft 365 Copilot. It pulls ahead most on free tier quality, setup effort and price per seat. That said, the better buy still depends on your own constraints — check the spec table below for the trade-offs.
| Spec | OpenAI ChatGPT | Microsoft Microsoft 365 Copilot |
|---|---|---|
| Price Per Seat | $20 | $21 |
| Security & Admin | SOC 2 + SSO | SOC 2 + SSO + audit |
| Setup Effort | 15 minutes | IT ticket |
| Free Tier Quality | Generous | None |
| Business Integrations | — | 100 |
| Data & Tool Connections | MCP + agent actions | MCP + agent actions |
| Context Window | 128–272K tokens | — |
| Where It Runs | Web + desktop + mobile | Web + desktop + mobile |
| Specs won | 3 | 1 |
| SquadScore | 77.1 | 64.8 |