Armstrong met Kristin Richard in 1997, and the pair married less than one year later. The couple had three children together before their divorce in 2003.
"(The divorce) was not pleasant; the girls were still in diapers," Armstrong said on ESPN documentary Lance.
"I will take all the responsibility for saying 'I'm out'. That was my MO at the time, still is a layer of that to me. She wanted to figure it out, but I just said, 'I'm out.'
"Then I had this relationship with Sheryl that lasted for years, and Kristin's going, 'Wait a minute, we just got divorced and now I'm reading in every news outlet in the world about my ex-husband, the father of my three kids, with this rock star.' It couldn't have been easy."
Richard strengthened focus on her Christian faith after the divorce, and spoke to the Christian Broadcasting Network about how she handled the separation.
"The path of sour bitterness, crusty resentment, and cold regret breeds generations of despair," Kristin said.
"The path of righteousness grants generations of peace, quietness, and confidence.
"Lance and I need to go forward honouring each other, because that's the way that we can still show our children that love is lasting and unconditional."
SHERYL CROW
During the same year of his first divorce, Armstrong began dating popular musician Sheryl Crow. The American singer-songwriter has released 11 folk records, and the pair proved a dynamic power couple.
However, Armstrong admitted he was not happy being part of a celebrity relationship.
"I had this relationship with Cheryl that lasted for years," Armstrong said.
"I so do not miss living with or loving or being in a relationship with anyone famous. In those situations, you can't get out. And then you're afraid to break the cycle and stay in. And I did it, I did it way too long. I should have said 'no I can't do this'.
"I'm really sorry, I should've said that a lot earlier. I should've been honest."
The star duo got engaged in September 2005, but then jointly announced their separation less than six months later.
"After much thought and consideration we have made a very tough decision to split up. We both have a deep love and respect for each other and we ask that everyone respect our privacy during this very difficult time," their statement read.
Crow had also formerly dated musician Eric Clapton and Hollywood actor Owen Wilson.
It was first reported Armstrong was dating New York fashion designer Tory Burch in March 2007, but the pair had allegedly already been seeing each other several months at that stage.
The couple parted ways a few months later, with the New York Post confirming their split in October that year.
A spokesperson for Burch described the split as "amicable".
KATE HUDSON
Armstrong briefly dated American actress Kate Hudson in 2008, the relationship lasting a few months.
Bizarrely, Hudson had also previously dated actor Owen Wilson before her fling with the cycling superstar. She also had a relationship with retired MLB star Alex Rodriguez for almost a year.
Hudson spoke about her sporting ex-partners — both of whom were embroil in doping scandals — to InStyle magazine in June 2014.
"Lance and Alex are phenomenal athletes who have made some bad choices and let a lot of people down," Hudson said.
"It's a decision they made for themselves and they've got to loathe it. I personally think that you make the choices you make and you should reap the consequences.
"People have a right to (feel betrayed)."
Armstong met Anna Hansen through his charity work in July 2008, when Hansen was working at a small not for profit organisation helping young adults with cancer, and less than six months later the cycling great announced she was pregnant. In 2010, the couple had a second child together, but did not get engaged until 2017.
Hansen and Armstong are still yet to officially get married, but have been together for nearly twelve years. Not even the infamous doping scandal could separate them.
"He definitely dated a few people before me. I've been his partner for about 10 years now and we have two kids," Hansen said during episode 2.