41 Charlie Squeen Fingerpaint - MyBoyJ


Upon seeing the word "winning" my first thought was Charlie Sheen and his infamous interview. Here we have his ponified counterpart, Charlie Squeen, discussing his addiction to sugar. Remember, he's not bipolar. He's bi-winning.
42 Gaming Princesses - Mari Delarock


The back legs look really bad because I still can't draw ponies sitting down yet. (Derp, I forgot to put wings on Celestia.)
43 EQD Training Grounds Day 08 - Blayaden


Pinkie pie isn't the only pony thats a master of Tic-Tac-Toe!
44 Midnight Chess - ImpCJCaesar


Silly Twilight doesn't know that to destroy a tower you need rocks!
45 Games - Pixernosse


46 The Winning Pony - Thanqol


Cloud Kicker is inherently the winningest
47 White plays first. - RandomCPV


48 This is not a game - NATGIII day 8 - Whatsapokemon


Two things in life are certain - death and die. The theme today was "Draw a pony playing a game/Draw a pony winning!" For Pinkie Pie I imagine quite a lot of life is a game. It was only going to be one panel, but I couldn't resist.
49 Doctor defeats a Dalek!- Or not so much... - Amber flicker


Dinky: "Daddy wins!" Dinky plays with her toys.
50 Gibbontake wins - PinkiePieFiesta


51 3rd EQD ATG Day 8 - Frostspear


So-ooo... on one hand, I'm away from home in Manchester in order to attend BUCK 2013. On the other, I fully intend to enter as many days as possible. With that in mind, have a shoddy picture of a sketch of Octavia cosplaying as Fiora Laurent, the Grand Duelist, from League of Legends.
52 Pinkie Plays iPad - BlueVanilla


Recently got a graphics tablet and wants to learn how to use it. This is my 1st fully digital artwork. From start to finish. My other works are mostly sketched on paper, which I can say is a lot easier than this graphics tablet. XD
53 A game she can excel at - Quint the Wanderer


Snowdrop should be happy that she can't see the monster she has pinned the tail on. (:
54 Sisters - Pio21


55 Winning At Shhh! - TheBaraclough


What, you thought she was kidding when she said she was the world champ? well I'll have you know she went through 74 grueling rounds of Shhh and braved the spotlight the entire time. This probably has been done before and in a much better way but I enjoyed drawing this and hope all of you enjoy it as well = ).
56 A winner is you! - David Lockwood


57 Chess - Cloudy


I miss my scanner...
58 Dicing with Dash - Chrisgotjar


Ended up having to rush this one nearer the end so the wings and cleaning up kind of almost never happened. (forgot the wings :I) Cleaning up needs loads more but hey outlines!
59 Twillight playing N64 - Varien Quill


60 Baschfire - Raedrob


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