About
Win Some Lose Some was written by Robbie Williams and Guy Chambers and released exclusively as a single in New Zealand on 13 March 2000, where it reached number seven and remained in the Top 40 for 21 weeks. Though not issued as a UK single, it became a fan favourite and was later included on the New Zealand edition of Greatest Hits (2004) in recognition of its enduring popularity.
The song reflects on young love and disillusionment, written in a conversational tone typical of Williams’ late-1990s storytelling. It draws partly on his memories of teenage relationships in Stoke-on-Trent, including an early girlfriend who introduced him to the guitar. Combining melodic optimism with lyrics about romantic frustration, it captures the singer’s recurring theme of learning through loss. The upbeat arrangement and rhythmic guitar work contrast with its bittersweet message.
It’s one of those songs about life teaching you lessons, about getting things wrong and carrying on. You win some, you lose some.Robbie Williams
The track opens with a brief spoken snippet by Nicole Appleton, Williams’ partner at the time, which adds a personal note but later became dated after their separation. Despite never being a UK single, Win Some Lose Some has appeared occasionally in setlists, particularly during New Zealand shows, where audiences often treat it as a local classic. Its lively production and straightforward sentiment mark it as one of the lighter moments on I've Been Expecting You.
Lyrics
We didn't think it'd last beyond summer
I met her father she met my mother
We didn't have anywhere else to go
She said to me when we grow older
Will we still need young love on
Our shoulders
Does it just fade away
Will we ever know
She touched my face and called me
Her lover
I never thought that I'd need another
Your cool suburban sun
You're foolin' every one
You win some you lose some
I didn't know what we had found
Just caught the bus and rode it to town
She wouldn't notice anything else but me
Your cool suburban sun
You're foolin' every one
You win some you lose some
Dancing at discos
And moaning at phone bills
Torremolinos and sun burnt in high heels
Swap it and sell it
And drop it and smell it
All those years ago
She touched my face and called me
Her lover
I never thought that I'd need another
Your cool suburban sun
You're foolin' every one
You win some you lose some
Your cool suburban sun
You're foolin' every one
You win some you lose some
Now it's gone, now it's gone,
You win some, you lose some
Now it's gone, now it's gone,
You win some, you lose some
Now it's gone, now it's gone,
You win some, you lose some
Now it's gone, now it's gone,
You win some, you lose some
Win some
Credits
-
Vocalist
Robbie Williams -
Songwriter
Robbie Williams, Guy Chambers