He was appointed as a judge in the Tel Aviv Magistrate's Court in 1972 and as a judge in the Tel Aviv District Court in 1977. He holds a Ph.D. in law from Hebrew University in Jerusalem. After retiring from the judiciary, Dr. Winograd was active as an arbitrator and chaired numerous public commissions.
Some of Dr. Winograd's most notable appointments include:
- Chairman of the Public Commission on the tuition of students in universities, recommended reducing rates gradually by up to 50%;
- Chairman of the Public Commission on pension arrangements;
- Chairman of the Public Commission regarding the military rank of (retired) Major General Yitzhak Mordechai, decided not to annul rank despite his conviction of sexual assault;
- Chairman of the Public Commission formed by the IDF to examine the sequence of events and available information regarding captured soldier Ron Arad;
- Chairman of the Inquiry Commission investigating the cable accident in the Israeli Air Force;
- Chairman of the Inquiry Commission regarding the replacement of body parts of IDF Squadron 13 soldiers killed in Lebanon;
- Chairman of the Winograd Commission investigating the Second Lebanon War and the events preceding it.