The Stampeders also signed free-agent veteran import defensive back Lin-J Shell, who most recently played with the B.C. Lions.
"These players possess considerable experience and provide us with depth in the secondary," Stampeders head coach and general manager John Hufnagel said in a release. "We know Dee from his first stint in Calgary and obviously our defensive co-ordinator Rich Stubler is very familiar with Lin-J from their time together in B.C."
Webb originally signed with the Stamps in 2009 and played one game for the team that season. He signed with the Toronto Argonauts in 2011 and was later traded to Hamilton.
In 42 career games, he has 109 tackles, nine special-teams tackles, four interceptions and one fumble recovery.
Shell, meanwhile, has 89 games of CFL experience in five seasons with the Argos and Lions. The two-time East Division all-star (2010, '11) has 280 tackles, 55 special-teams tackles, eight interceptions, two forced fumbles and nine fumble recoveries over his career.
Also Wednesday, the Stampeders released import defensive back Jonathan Hefney and import receiver Tim Hawthorne. The Ticats released defensive back Arthur Hobbs and wide receivers Spencer Armstrong and Jay Diston.