Here is the full list of all 46 Mr. Driller DrillLand trophies - there are 33 bronze, 9 silver, 3 gold and 1 platinum.
Reach the goal without collecting enough Golden Statues in Drindy Adventure (Classic)
Get your blood sucked by bats 30 times in Horror Night House (Classic)
Clear Horror Night House LEVEL 2
Clear Star Driller LEVEL 2
Collide with a white comet in Star Driller (Classic)
Meet Tobi Masuyo in Star Driller (Classic)
Get sucked into a black hole in Star Driller (Classic)
Clear The Hole of Druaga LEVEL 2
Clear World Drill Tour LEVEL 2
Foil Dr. Manhole's plan
Clear Drindy Adventure LEVEL 1
Clear Star Driller LEVEL 1
Clear World Drill Tour LEVEL 1
Clear Horror Night House LEVEL 1
Clear The Hole of Druaga LEVEL 1
Enter Drill Land
Earn all game trophies
Clear World Drill Tour LEVEL 3
Clear Star Driller LEVEL 3
Clear The Hole of Druaga LEVEL 3
Clear Horror Night House LEVEL 3
Clear Drindy Adventure LEVEL 2
Clear Drindy Adventure LEVEL 3
Clear Dr. Manhole Strikes Back
Clear Dr. Manhole Strikes Back twice
Obtain Title Stamps from all Classic attractions on LEVEL 1
Obtain Title Stamps from all Classic attractions on LEVEL 2
Obtain Title Stamps from all Classic attractions on LEVEL 3
Obtain Title Stamps from all Classic attractions on LEVEL SPECIAL
Obtain Title Stamps from all Classic attractions on every level
Clear World Drill Tour LEVEL 1 (Classic) with every character
Dig 8848 meters in World Drill Tour (Classic)
Get caught by a UFO in Star Driller (Classic)
Clear The Hole of Druaga LEVEL 2 (Classic) using warp only once
Use Dristones to defeat at least 10 common baddies in The Hole of Druaga (Classic)
Collect all Golden Statues in Drindy Adventure LEVEL 3 (Classic)
Destroy all boulders in Drindy Adventure LEVEL 1 (Classic)
Use three support items at once and clear a Classic attraction
Unleash Usagi in Classic (collect Driller Cards 7 and 30)
Earn one million bits in Classic
Collect all Movie Theater movies in Classic
Collect all Music Palace songs in Classic
Purchase all Item Shop items in Classic
Obtain all Drill Land goods in Classic
Collect all Driller Cards in Classic
Play two modes on Enter Together