As was the case for the previous installment of this series, there were not very many walkoff home runs hit by Cubs players in this five-year span, just seven of them.
One of them was a particularly memorable big fly during a pennant race. I’ll get to that, but let’s start at the beginning.
May 6, 1986: The Cubs trailed 5-2 in the fifth inning, but took a 6-5 lead into the eighth, only to blow it and the game went tied into the last of the ninth. Leon Durham led off that inning with a home run off Tom Niedenfuer and the Cubs defeated the Dodgers 7-6.
July 2, 1986: With one out in the bottom of the ninth, Davey Lopes — then 41 years old — homered to give the Cubs a 5-4 win over the Montreal Expos.
September 9, 1986: The Cubs went behind 6-1 in the fourth inning against the Phillies. They tied it up in the seventh and had the winning run in scoring position in the ninth, but a double play ended that inning. Keith Moreland singled with one out in the 10th and Leon Durham homered [VIDEO] for an 8-6 victory.
May 21, 1987: Another unlikely candidate for a walkoff homer, Bob Dernier, hit one with two out in the ninth after Lee Smith had one of his 12 (!) blown saves that year in the top of the inning. (If you’ve ever wondered why the Cubs traded Smith, that’s why.) The Cubs beat the Reds 8-7. It was the only walkoff homer Dernier hit as a Cub, though he hit another one in 1989 as a Phillie — and an inside-the-park walkoff at that!
June 8, 1987: Another blown save for Smith, another walkoff homer for the Cubs. This one was a two-run shot by Manny Trillo.
June 22, 1987: The Cubs blew an eighth-inning lead in this one, but it wasn’t Smith’s fault this time. Andy Van Slyke hit a two-run homer off Jamie Moyer to give the Pirates a 2-1 lead. But in the last of the ninth with a runner on, Keith Moreland homered off former Cub Rick Reuschel for a 3-2 victory.
July 30, 1989: The Cubs had a 4-2 lead going into the seventh, but the Mets tied it on a two-run single by Keith Hernandez off Mike Bielecki. Jerome Walton singled with one out in the ninth, and one out later Mark Grace came to bat against Randy Myers [VIDEO].
The Cubs were still in second place in the N.L. East after that win, but it was their 10th win in their last 13 games and helped send them on the way to a division title.