The world number 27 made the quarter-finals at the All England Club in 2012 and secured a 6-3 6-3 victory against John Isner, who can lay claim to his own unique piece of Wimbledon history.
Isner, ranked 11th in the world, won the longest match of all time at the famous grass-court grand slam four years ago, defeating Nicolas Mahut in a fifth set that totalled 138 games.
On a day when the players learned the identity of their first-round opponents at Wimbledon, it was Kohlschreiber who received a late confidence boost with his second win at The Boodles, having also beaten Fabio Fognini on Wednesday.
Fognini, meanwhile, suffered another loss as he was defeated 6-3 6-3 by Marin Cilic.
The Italian is the 16th seed at Wimbledon, which begins on Monday, though he has never gone beyond the third round there.
In the final game on court, Jerzy Janowicz was taken the distance by Jack Sock before triumphing 6-3 3-6 10-8.