There have been a few memorable times he hasn't used a guide. An easy tell is when there's a puzzle boss or just some kind of enemy where you have to think outside the box to defeat it and it doesn't click with Phil, the sense of dread in his voice becomes palpable, ultimately culminating in babyman.exe activating.
A good example of that is when he was playing the RE3 remake and he couldn't figure out how to win the earlier boss fight with Nemesis, the one where he would jump around the cars before climbing the tower. Phil whined like crazy, threw a temper tantrum and paused the game and folded his arms saying he wasn't going to keep playing until sometime told him how to beat the boss.