1950s / 1960s: 1962 Topps #170 Ron Santo This is a very young looking Santo at Candlestick Park in 1961. The 1962 season was his third big-league season and he experienced a bit of a junior jinx (if there is such a thing). His batting average dropped from .284 to .227 and he hit six fewer homers. He did knock in the the same number of runs as in '61, 83, so despite the drop in average and power, he was still producing runs. A durable diabetic, Santo played in all of the Cubs 162 games.
1970s: 1978 SSPC #260 Dennis Lamp This card comes from the 1978 SSPC book which I've detailed here and here. The 1978 season saw Lamp in the starting rotation for the entire year. His final numbers were an interesting mix...his record was 7-15 while his ERA was a respectable 3.29 (best among all Cubs starters). The Cubs were shut out in six of his losses and scored only one run in six more.
1980s: 1989 Star #10 Jerome Walton Notice the error on this card, listing Walton as a member of the White Sox. This card is one of eleven in the Star 1989 Walton set. It's also one of two in the set that have nothing on the back. I guess that as a rookie, Star ran out of things to say about him after the first nine cards.
1990s: 1997 Big League Chew Billy Williams The Big League Chew Alumni Series has three cards in the set, the other two being Juan Marichal and Brooks Robinson. The cards were available by mailing in proofs of purchases. Since autographed cards were the only ones they gave, I know that the signature is authentic.
2000s: 2002 Fleer Tradition #290 Matt Stairs Stairs came to the Cubs for the 2001 season to replace Mark Grace until super-prospect Hee Seop Choi was ready. His numbers for the season were very average (17 HRs, 61 RBIs, .250) and the Cubs didn't re-sign him for the 2002 season. Instead, Stairs spent the year with the Brewers. It was another of a long line of stops in Stairs career...check out this from his baseballreference page
...a pretty long line of uniforms and numbers.