Following his first degree he won an SERC scholarship for doctoral study in the field of information theory and error-correcting codes under the supervision of Rodney Goodman.

[25] In 1984 Winfield resigned his lectureship and founded, with Rod Goodman, Metaforth Computer Systems Ltd, with the aim of commercializing the Forth machine.

[32] From 2006 to 2009, with Noel Sharkey, Owen Holland and Frank Burnet,[33] Winfield led public engagement project Walking with Robots.

[34] The project was designed to encourage children into science and technology careers, and to involve the public in discussions about robotics research issues.

with Maja Pantic, Samantha Payne and Christian List chaired by Claire Craig,[39][19] lectures and Q&A with Raja Chatila at the Royal Institution,[40][41] talks and Q&A with Ron Arkin at 'Smarter Together': Why AI Needs Human-Choice?

[54][55] He served as an expert advisor to the NHS Health Education England Topol Review Preparing the healthcare workforce to deliver the digital future.

[58] He is a member of the initiative's executive committee,[59] and chaired the working group that drafted IEEE Standard 7001-2021 on Transparency of Autonomous Systems.