On 17 May 2004 Gabrielle released her fourth studio album Play To Win. It reached number 10 in the UK and was the 191st best-selling album of 2004. "Stay the Same" is the first single from her fourth studio album Play to Win. The single managed to peak at number twenty in the UK Singles Chart, helping the album peak inside the UK top ten. "Stay the Same" was, however, her lowest charting single in eight years, albeit her tenth consecutive top twenty hit. The second single "Ten Years Time" was the second and final commercial single from her fourth studio album Play to Win. The song is Gabrielle's lowest peaking single to date and her first to miss the UK top 40, peaking at 43, only spending a week inside the top 75. One further single was released to promote Play to Win but no video or commercial release was given to the song ("You Used to Love Me"). A supporting UK tour followed. The track "Sometimes" from this album features on the Love Actually film soundtrack.[9]
In 2007 she released a new single, "Why", which she performed on The National Lottery show on 19 September, as well as many other TV slots. "Why" did not reach the UK Top 40. On 1 October 2007, fifth studio album Always was released. The album received positive reviews from music critics and was released on 1 October 2007 in the UK, being preceded by the single "Why" on 24 September 2007. Always entered the UK Albums Chart at number 11, just 12 copies from entering at number number 10. Always entered the UK R&B Album Chart at number 4. It included a version of the song "Why" that featured Paul Weller. The final single from the album "Every Little Teardrop" was released; however, it failed to chart.
Gabrielle set off on a sell out UK tour of fourteen dates through February 2007. Critics gave positive reviews on her performances. Following the relative disappointment regarding the singles "Why" and "Every Little Teardrop" Gabrielle stated: “If people don't like that song then I'll find one that they do like because I have done it before and I'll do it again. That old saying ‘if at first you don't succeed, try and try again', well that's me, because I'm a fighter not a quitter.”[10] Gabrielle headlined the 'Zermatt Unplugged' music festival in April 2008, along with Alanis Morissette.[11] In addition she headlined 'Birmingham Pride' in 2008.[12] In May 2008, Gabrielle won an Ivor Novello award for Best Song Collection. In a recent interview Gabrielle revealed that she has begun writing songs for a mystery new artist. She said, "It was really good to get asked to do something like that, as the pressure isn't on so much". But also states that it is not the end of her performing and recording career, "I look up to people like Dionne Warwick and Madonna, for managing to keep careers going for so long. I'm not that far behind Madonna, really," says Gabrielle, 38. "It'd be great to be making music like those old birds".[13] Gabrielle was also Al Green's special guest on the UK dates of his 2008 tour.