Raonic and Kyrgios were both ousted in three sets by Mackenzie McDonald and fellow American qualifier Bradley Klahn respectively, but 10th seed Stefanos Tsitsipas was able to progress courtesy of a 7-6 (7-4) 4-6 6-4 success over Gael Monfils.
"He can win bigger tournaments and do all these things", he added.
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The Shanghai Masters has been a particularly unhappy hunting ground for Kyrgios over the years, with this being the fourth year in a row that he has stoked controversy at the competition.
Last month umpire Mohamed Lahyani was suspended from his next two scheduled tournaments after trying to encourage Kyrgios during a match at the US Open.
Tiafoe, however, lost to Matthew Ebden 3-6, 6-4, 6-3.
The fallout to his latest on court drama was once again met with severe backlash from social media, many of whom believe perhaps professional tennis isn't for him.
"He needs to do like any other player needs to go through in order to be successful". Scheduling is huge for him.
Woodbridge's comments come after Kyrgios's prolonged exchange with the chair umpire at the Shanghai Masters during his first round defeat to American qualifier Bradley Klahn. "He gets exhausted and then it's regrettable for him".
"I think we're two very different characters", said Kyrgios following his loss to the Swiss at the US Open.
"I could literally just say I couldn't play after that because I just felt put down".