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Desmond’s Timeline from 1995-2001

1989
Desmond begins dating Ruth. ("Catch-22")

1995
Celtics win the Scottish Cup ("Catch-22")
A week before his wedding to Ruth, Desmond gets drunk and is found in the street by Brother Campbell. Desmond joins the monastery. ("Catch-22")
Upon being expelled from the monastery, Desmond meets Penelope Widmore. ("Catch-22")
The vintage of the wine bottles and Ruth's mention of Celtic winning the Cup date this flashback to 1995, where he first meets Penny. Desmond's later flashback where he breaks up with Penny takes place in 1996. Normally wine is dated based on the date of the grape harvest, and Cabernet Sauvignon is usually aged in barrels for years before being released, so the date on the bottle is likely a production error meant to show the date of the flashback and not a realistic vintage date.
Desmond is in a monastery in Eddington, Scotland in 1995.
RUTH: We dated for six years, and the closest you ever came to a religious experience was Celtic winning the cup.
DESMOND: OK, yes, I was scared about the wedding, so I had a few pints too many, maybe I, I raised my eyes, and I asked am I doing the right thing, and that's the last thing I remember. And when I woke up, I was lying on my back in the street, and I dunno how I got there and, there was this man standing over me, Ruth. And he reached out his hand and he said to me, can I help you brother. And the first thing I noticed was the rope tied round his waist, and I looked at him and I knew, I knew, I was supposed to go with him. I was supposed to go with him, I was supposed to leave everything that mattered behind, sacrifice all of it, for a greater calling.

Either way if we go with the fact that this all took place sometime after May 1995 it does not add up for when Penny & Des got together by what is said in Flashes before your Eyes!!

1996
Desmond proposes to Penny, and applies to Charles Widmore for a job. ("Flashes Before Your Eyes"), (Official Lost Podcast transcript/February 20, 2007)
DESMOND: No, sir. I came here to ask for your daughter's hand in marriage. We've been together 2 years now and Pen's moving in and I love her. Your permission would mean everything to me.
According to the producers, Desmond did really travel back in time, and the events he relived occurred in 1996. (Official Lost Podcast/February 20, 2007)
How can Desmond and Penny have been together for 2 years when they did not meet until after May 1995????

1999
April 4th - Desmond completes his prison sentence and is dishonorably discharged from the military. Charles Widmore immediately attempts to bribe Desmond to run away and forget Penelope Widmore. ("Live Together, Die Alone")

2001
Desmond meets Libby at a coffee shop shortly after arriving in the United States (Los Angeles?). She loans him her boat. ("Live Together, Die Alone")

Penelope tracks down Desmond at the stadium. ("Live Together, Die Alone")

Jack meets Desmond at the stadium ("Man of Science, Man of Faith")

Desmond begins the boat race in Libby's boat. ("Live Together, Die Alone")

Desmond arrives on the Island and begins pushing the button with Kelvin Joe Inman. ("Live Together, Die Alone")