I don't think that I played the Cafe games the 1st year/season I joined, but I finally won Pick 3!
IMO Trivia Time Trial is probably the hardest. But I'm a trivia geek & not many people play the trivia game. I won that back when the game play was slightly different & the computer that I had was a lot faster. I don't even play that anymore because my computer is SO slow. It's the only game that I've won the title for the year.
I'm bad at picking games so Lucky Ladders (and Pick 3) are always very difficult for me. My only Lucky Ladders win was kinda cheap. It was at the end of the season & not a lot of people played that week. I won with like a 3 or 4 rung ladder.
I also find Matchup Meltdown hard, but I finally made the cut on that last year. I used my bye week in week 1 for the 1st time, and that really helped me out.
Blackjack is total luck & I've been lucky there at least once.
Pick 3 was the final & elusive "game icon" that I needed. I've come real close before. I think I came in 2nd one week. One week I had 2 games almost exact, and the exact score in the 3rd game...but with the wrong winner! I'm very happy to finally win what to me is the hardest Cafe game to win.