I mean in the playoff era 1969 to present. (I'm 61). My choice is 1986. For me that Game 7 clincher over Angels was the sweetest to me. From being down 3 games to 1 after the heartbreak of Schiraldi hitting Downing in the 9th to tie it then to lose in extra innings just killed me. Thank God for Baylor and Hendu. They saved our butt. My dad was alive and he had a quite a smile on his face. He could be a Cynical Sox fan(He passed away in 1999) I went out to celebrate at a Philly area bar. Many New England College students and transplants were there. I can honestly say I was never happier at the time as a Boston sports fan. (OK maybe Celts beating Lakers in 84 and Bobby Orr's goal in 70) but you get the feeling I had. They were all great 75, 86, 04, 07, 2013 and 2018, but other then October 20th 2004 and October 27th 2004, that was the sweetest Moment for a Red Sox pennant clincher. There's more to do. I hope they play the Brewers. GO RED SOX!