The 80s band Mike + the Mechanics has five hits in My Weekly Top 10 countdown. They have a chart span of 33 years from their first single to hit the top 10 to the latest.
1985 - Silent Running (#7)
1985 - All I Need is A Miracle (#3)
1985 - Taken In (#1)
1989 - The Living Years (#1)
2017 - Don't Know What Came Over Me (#4)
Here's the video of the song. It already has 49,181 views.