The Rosmalen Grass Court Championships final saw Adrian Mannarino end his ATP title drought with victory over Jordan Thompson.
Felix Auger-Aliassime was denied a first ATP Tour title by Matteo Berrettini, who won the Stuttgart Open final.
Matteo Berrettini and Felix Auger-Aliassime will meet in the Stuttgart Open final, but the semi-finals are yet to be resolved in Den Bosch
Felix Auger-Aliassime will battle with compatriot Milos Raonic for a place in the final of the Stuttgart Open.
Alexander Zverev is 165 places above Dustin Brown in the rankings, but lost to his compatriot on home soil in Stuttgart.
Runner-up at the 2018 Stuttgart Open, Milos Raonic continued his comeback from injury by beating Jo-Wilfried Tsonga in Germany on Wednesday.
Three-time grand slam champion Andy Murray is "progressing all of the time" but is prepared to be patient rather than rush a singles return.
Making his grass-court debut on the ATP Tour, Canadian teenager Felix Auger-Aliassime was far too good for Ernests Gulbis.
Not since the ATP world rankings were first established in 1973 has there been an older entrant to the top 10 than Italy's Fabio Fognini.
As Alexander Zverev prepared to start his Stuttgart Open campaign, his brother Mischa lost to Jo-Wilfried Tsonga in the first round.