The Tigers’ uniform Old English "D" made its debut in 1896, when the club played in the Western League. Its first appearance took place on April 28 of that year, during the club’s home opener at Bennett Park, located at the corner of Michigan Street and Trumbull Avenue.
The club first wore an Old English "D" on their caps in 1905, though the “D” on the cap and the “D” on the uniform didn’t perfectly match. Todd has written about this a number of times, including HERE, HERE, and HERE.
The Tigers' “D” has been a staple of the team's visual identity since 1904, when it was first featured on their road uniforms. The D morphed and sometimes disappeared entirely in the early 20th century.
The 1930-33 clubs wore a script "Detroit," both at home and on the road. These four seasons represent the longest continual stretch that the franchise did not sport an Old English "D" in its history.
Todd Lukas of Uni Watch has also written about teams with mismatched cap and uniform logos. You can read one such article HERE.