Court documents from the former couple's child custody battle revealed Thompson's financial report included entries totaling $65,724.56 under sections titled Khloe K, Kendall Jenner, Inc. and Kim K West, according to Radaronline.com
And Craig claimed Thompson only saw his son a total of nine times from the day Prince was born to November 2018.
During a January 28, 2019 deposition, Thompson was questioned by Craig's attorney Craig Bridwell about a $42,857.68 entry on August 15, 2018 filed under Khloe K.
Thompson was also pressed on an August 24, 2018 entry labeled Kendall Jenner, Inc for $14,886.88 with a memo listed as 'vacation.'
$7,980 was processed on November 6, 2017 under Kim K West with a note stating 'Birthday Gift'.
During that period, he reportedly spent a total of $126,890.11 for dining out at celebrity hotspots in Los Angeles.
He also coughed up 'about $129,000' on such lavish expenditures as private jets, high-end cloths and luxury cars.
Craig even mentioned how she feared that Prince would eventually be embarrassed that he wasn’t living the same lifestyle as his half-sister, True Thompson - the daughter of Thompson and Kardashian.
'I would like for Prince to just not feel some type of complex,' Craig said according to the documents.
'Like if he’s playing with his sister and he’s not wearing, like, designer clothes and things — luxury that Tristan can give him that I can’t.'
Thompson was previously paying $15,000 per month in child support, but Craig argued that was 'much less' than what she should be receiving, per California guidelines.
In May, he agreed to $40,000 a month, and $200,000 in retroactive child support.
Meanwhile, Kardashian took to her Instagram story on Tuesday evening, to address reports that she was Thompson's mistress while the NBA player was dating the then-pregnant Craig.
The 34-year-old KUWTK star made her statement after the release of court documents from Jordan, after which Khloe stated that she was 'disappointed' about even needing to post the statement yet still apologised to his scorned ex.
She then went on to reveal details of the early days of her relationship with Thompson which started in 2017, in which she divulged intimate explanations of what she was told by the love rat sportsman and his inside circle.
Khloe and Tristan's fractious relationship ended in tatters in February after it was alleged than he was caught kissing her sister Kylie Jenner's best friend Jordyn Woods during a house party, in a devastating blow to the star.
The infidelity comes after the basketball ace is said to have cheated on Khloe on a number of occasions while she was expecting their 14-month-old daughter True.
Since escaping the doomed relationship, Khloe has now been incensed to address ongoing claims that she was in fact, the other woman for Tristan while Jordan was expecting their two-year-old son Prince Thompson.
Khloe was named as his 'mistress' in a child support request filed by Jordan in November. She claimed when she learned about the relationship, she moved out of the Cleveland home she shared with the athlete, and back to Southern California.
Taking to Instagram on Tuesday, Khloe penned a lengthy prose to address such rumours while also chronicling the start of her now-defunct union with Tristan.
She wrote: 'My truth is: I met Tristan because HE CHOSE to go on a blind date with me. A mutual friend set us up... After going on some dates, Tristan told me that he had an ex that was pregnant [referring to Jordan Craig]...
'Obviously, I was reluctant about us continuing to date or start a relationship, He pleaded with me that the relationship was over long before we met. He had me talk with his most inner circle...
'He showed my physical p(r)oof (correspondence between the two) and had me on calls with his lawyers to prove his point...
'His best friends, business associates and even his mother told me, him and his ex were broken up before we met...
'This is my truth! The truth I believed and trusted. If for any reason this is NOT in fact the truth, I am so completely and utterly sorry that TRISTAN and his inner circle would lie on something like this!...
'I pray my truth is in-fact that. Lord knows I pray but now, I really don't know what to believe. Truthfully, from the deepest parts of my soul I am sorry!...
'I'm sorry for any pain that has been created either way. No woman deserves to go through anything like this! This is my TRUTH' .
Radar previously reported that a child support request from last November, saw Jordan state that she was romantically-involved with the Cleveland Cavaliers center, and became pregnant with his child before his union with Khloe.
Jordan, a Los Angeles native, said when she learned about the allegedly illicit relationship, she moved out of the Cleveland home she shared with the professional athlete, and back to Southern California.
She claims she reunited after Tristan 'tried to get back together on numerous occasions,' insisting 'he would change for our family.' Jordan told the court she moved out of the LA home they shared amid Tristan's 'partying' and affairs.
It appears she was alluding to Khloe in the comments as she was seen recalling how she saw shots taken by the paparazzi 'with one of the women I previously confronted him about, and whom Tristan had denied even knowing.'
Images of Khloe and the NBA player began to arise in August and September of 2016, when the pair was seen clubbing in Los Angeles and vacationed in Mexico.
In harrowing words in regard to her personal situation, Jordan explained: 'Their relationship went viral and everything took a turn for the worst...
'Every day several articles were published worldwide mocking my new unfortunate reality and my pregnancy would now become one of the most popular gossip headlines due to the woman Tristan was now publicly dating during my pregnancy.'
Jordan said Thompson's affair had a critical impact on her pregnancy with son Prince, who was healthy when she gave birth to him in December of 2016.
She said: 'This brought an enormous amount of negative, unwanted attention and stress into my life, and more critically, into my pregnancy...
'My obstetrician ordered me to be on bed rest due to high levels of stress that eventually caused me to have serious pregnancy complications.'
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