1980s: 1984 Team Issued #18 Richie Hebner This card came from a set sponsored by 7-UP that the Cubs gave away on August 8, 1984. The Cubs were on a roll, and won that day, completing a four game sweep of the Mets and boosting their division lead to 4½ games. Hebner didn't play that day, so his contribution to the team was to cheer loudly from the dugout.
1990s: 1991 Classic #153 Derrick May May has two cards in the 1991 Classic set, which I find interesting since he played in just 17 games for the Cubs in 1990 and 15 more in 1991. All of his 1991 appearances were as a September call-up and he hit just .227 in those 15 games.
2000s: 2006 Topps #623 Geovany Soto Topps included Soto in the 2006 set, figuring he would make the team after a brief call-up the previous September. It didn't turn out that way, as most of 2006 was spent in AAA.
2010s: 2013 Team Issued Season Ticket Holders #23 Ryne Sandberg The RNG was liking the team issued cards today and grabbed a second one. This was given away at the Cubs 23rd home game of the 2013 season on May 17. The Cubs were again playing the Mets, but this time there was no pennant fever for either team. The Cubs lost 3-2, dropping their record to 17-24 and they were already ten games out of first place.