|1981 Topps #445 Ellis Valentine|
The first actual cards I have found with batting helmet masks is 1981 Topps with Ellis Valentine and Ron Roenicke using football masks cut in half and bolted on the batting helmet.
Starting in the early 1990's the more familiar jaw guard called the "C-Flap"started to appear on cards. Terry Steinbach has several cards from 1989-1991 wearing one. David Justice has a few cards in 1991 with a guard on his helmet. After being hit in the head for the second time in 1995, Kevin Seitzer took to wearing one for the rest of his career and can been seen with one on cards from 1996-1997, his son Cameron Seitzer can be seen with the guard on his 2012 Topps Pro Debut card. Terrence Long has several 2001 cards showing a good side view of the guard and Josh Willingham has one on his rookie card. Most recently Marlon Byrd is pictured with the guard on his 2012 Topps Tier One autograph cards and Astro's Prospect Chris Wallace (full story here) has worn something close to the Charlie Hayes model since getting hit in college.
1981 Topps #37 Gary Roenicke 1989 Donruss Baseball's Best #323 Terry Steinbach
2001 Topps #278 Terrence Long 1991 Score 100 Rising Stars #45 Dave Justice
1997 Pinnacle #79 Kevin Seitzer 2012 Pro Debut #216 Cameron Seitzer
2003 Bowman #324 Josh Willingham 2011 Bowman Sterling #CW Chris Wallace