#2 Conor McGregor vs. Joseph Duffy: Cage Warriors 39: The Uprising (27th November, 2010)
This matchup marked Conor McGregor's Lightweight debut, and saw him lose by submission via an arm-triangle choke. His opponent Joseph Duffy who, much like McGregor eventually went on to compete in the UFC, was incredibly cautious when it came to engaging with the heavy-handed Notorious One in the pocket.
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McGregor kept pressuring Duffy against the fence, before the latter landed a beautifully-timed low single leg takedown--dragging McGregor to the mat. Duffy transitioned to side control and then almost immediately locked up the arm-triangle choke--forcing McGregor to tap and ending the bout in Round 1.
A similar pattern in both of McGregor's losses was that he got a bit too wild when it came to the grappling realm, and needless to say, paid a heavy price. In the fights that followed, McGregor would eventually tone down his flailing grappling movements and choose to adhere to the basics of BJJ and wrestling. The discipline which these losses instilled in Conor McGregor would prove to a blessing in disguise for him in his UFC 189 fight against Chad Mendes for the Interim UFC Featherweight title.
Despite being taken down to the mat by Mendes, McGregor stayed calm and refrained from flailing like a fish out of water--unlike his fights against Sitenkov and Duffy. McGregor would go on to stop Mendes by way of strikes--and the rest, as they say, is history...