Unreal Tournament III

This trophy can be rather time consuming, but you will get part of it done just from playing campaign. You can grind this (as well as the VCTF and Warfare plays) actively or automatically, whichever you would prefer. Doing it actively is slightly faster, but if you do it automatically you can do other things during the time or leave it overnight.

Active Method

Suggested Setup
Gametype: CTF
Map: Reflection (Smallest/Easiest Map IMO)
Mutators: Speed Freak

Playing in instant action with no bots, simply run to the enemy base, drop your translocator beacon, then run back to your base. Once you cap the flag warp to your translocator spot and drop another, then cap the flag again. Repeat once more to win the match. Repeat this procedure until you reach 100 match plays.

Automatic Method

Suggested Setup
Gametype: CTF
Map: Reflection
Mutators: Speed Freak
Bots: 1 Godlike bot
Must be played in Multiplayer, not Instant Action.

With the game set up like this, it will be you versus 1 Godlike level bot. If you leave you controller along the bot will simply run to your flag and capture it over and over again. Plug your controller in so that it doesn’t shut off then let the game sit. The bot will continue to win games and the games will start automatically, allowing you to leave the game running while the bot completes games.