Starting this list with anime from winter 2008-2009 because I happen to cross upon the list while searching for the winter 2009-2010 lineup. (Descriptions are quoted from AniDB.)

Maria-sama ga Miteru 4
Life goes on for the ladies in the Yamayurikai. On the one-year anniversary of Sachiko and Yumi becoming soeurs, Yumi receives a difficult task from Sachiko: to finally acknowledge someone as her younger sister.
Slayers EVOLUTION-R
In the universe of Slayers, the supreme being is neither good nor evil, but is called the Lord of Nightmares, who created everything, and who is said to “shine like gold on the Sea of Chaos.” Later, it is revealed that the Lord of Nightmares is in fact the Sea of Chaos itself. Four pillars rise out of the Sea of Chaos, and each supports its own world. Since the Sea of Chaos comprises the Lord of Nightmares’ body, the worlds likewise spring from her. In Slayers Next, the Claire Bible confides that if the worlds are destroyed and returned to chaos, the Lord of Nightmares can return to her true form (although why she created the four worlds in the first place has not been revealed, neither by the novels nor the author himself).
White Album
Out of curiousity. XD;
Fujii Touya, a college student, is dating a rising idol singer named Morikawa Yuki. There are numerous challenges to the couple’s relationship from the other people at Fujii’s college, Morikawa’s work, and elsewhere.
Then some fall 2009 anime:
Kobato
Kobato is sweet and perky girl, but also extremely naive about the world around her. She has a “mission”, which is to fill a mysterious bottle of hers with the suffering from people’s hearts so her wish to go a certain place that she desires to go can be granted. However, she must not fall in love with a particular boy she works with and whose heart she must heal.
Yumeiro Patissiere
Adaptation of Natsumi Matsumoto’s shoujo manga Yumeiro Patissiere (Dream-Colored Pastry Chef). The manga, which premiered in September 2008, tells the story of 14 year old Ichigo Amano, a clumsy girl who dreams of becoming a pastry chef. She draws closer to fulfilling her dream when she enrolls in the St. Mary Academy culinary school and meets a tiny “spirit of sweets.”
I have already downloaded about 2 episodes of this. Only the lack of free space has kept me from downloading the rest that are already subbed.
White Album Final
Of course, from the winter 2009-2010 lineup:
Durarara!!
The author Narita and illustrator Yasuda Suzuhito’s “distorted love story” is set in Ikebukuro, Tokyo, and revolves around an ensemble cast including street thugs, high school students, a female radio host, an underworld doctor, a young information vendor, and a headless Irish fairy.
Harukanaru Toki no Naka de 3
Just for the sake of completing it.
Katanagatari
The legendary swordsmith Shikizaki Kiki made 1000 swords in his career. The more swords a state had, the greater success they had in the wars. When the Shogun emerged victorious, he collected 988 of the swords…but those were just practice.
The final twelve swords were the pinnacle of his career. Each of them has powers so extraordinary, one man could defeat small armies.
Shogunate strategist Togame has been ordered to recover them. She first hired a ninja…but the worth of the swords is so great the entire ninja clad defected the moment they recovered one. Then she hired a swordsman…but he kept the sword for himself.
Her last hope is Shichika, the seventh and last practitioner of the Kyotoryuu — No Sword School. He and his sister live on an island cut off from civilization — they have no need for money. His sword school does not use swords — he would not want the swords for himself.
So why should he help her?
“Because you will fall in love with me.”
Those are the titles I’m interested in seeing so far. There are still more from other seasons that I didn’t include anymore. Please recommend what else from this season that I should see.