"Do the tones of the trumpet and oboe even match?"
Right now, you are probably looking at this page while thinking just that, aren't you?
The "brass instrument trumpet" and the "woodwind instrument oboe" are a combination of instruments that are completely different in their sound production mechanism, tone color, and volume.　
Your question is surely one that others who have seen this page also have.　

June 2024, the 1st Duo Recital.
In the surveys collected from the audience after the performance, there was an abundance of voices from people who, perhaps unexpectedly (?), enjoyed the resonance created by this combination of instruments, with comments like "I was surprised at how well they matched, more than I imagined" and "The tones of the trumpet, oboe, and piano blended together and resonated throughout the hall."
Why don't you also come and listen to this mysterious combination?

The 3rd Trio Recital this time will feature numerous masterpieces that color the stories of various films. We will deliver familiar songs from famous movies that you have seen or heard somewhere, performed with seven types of instruments: oboe, oboe d'amore, English horn, trumpet, cornet, flugelhorn, and piano. Please look forward to what kind of tone these well-known songs will have with this ensemble.

【Performers】
■Sota Sakaguchi (Trumpet, Flugelhorn, Cornet)
■Shunsuke Ota (Oboe, Oboe d'amore, English horn)
■Sayuri Hozumi (Piano)

【Program】
■Harry Potter Medley (from the movie "Harry Potter")

■Friend Like Me (from the movie "Aladdin")

■Merry-Go-Round of Life (from the movie "Howl's Moving Castle")

■He's a Pirate (from the movie "Pirates of the Caribbean")

■Nuovo Cinema Paradiso Medley (from the movie "Nuovo Cinema Paradiso")

■Merry Christmas Mr. Lawrence (from the movie "Merry Christmas, Mr. Lawrence")

■New Genesis (from the movie "ONE PIECE FILM RED")

■Kamado Tanjiro no Uta (from the movie "Demon Slayer: Kimetsu no Yaiba")

■Garnet (from the movie "The Girl Who Leapt Through Time")