IND DEP CTLR FAILED TO COORDINATE A FLT OF 4 A10 MIL ACFT WITH THE IND ARR SECTOR CAUSING A LOSS OF SEPARATION WITH AN ACR JET DSNDING INTO IND ARPT.

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WHILE WORKING E DEP/S A MIL ACFT CALLED WITH A BROKEN; UNREADABLE XMISSION. ABOUT 20 SECONDS LATER; MIL ACFT CALLS AGAIN. I ASKED IF THAT WAS ACFT #1 CALLING IND APCH. THEY ADVISED THAT THEY WERE VFR AT 9500 FT NBOUND 20 MI E; 25 MI N OF R3401. I ASKED WHAT ALT THEY WERE LEAVING AND THEY SAID LEVEL AT 9500 FT VFR. I ISSUED A SQUAWK CODE OF XYZA AND TOLD THEM TO MAINTAIN VFR. I IMMEDIATELY CALLED ZID; MIE SECTOR; FOR ACFT #1 WAS GETTING CLOSE TO THEIR AIRSPACE. I ADVISED MIE THAT JUST TAGGING UP AT THE HOMAR INTXN ON A CODE OF XYZA; WAS A FLT OF 4 A10'S STILL VFR AT 9500 FT. MIE ASKED IF I HAD DEPARTED HIM. I SAID NO AND TOLD ARR DATA TO 'DM.' ACFT #1 TAGGED UP AND I STARTED THE FLASH TO ZID. THE CTLR ASKED AGAIN IF HAD ISSUED THE CLRNC YET AND I SAID NO. HE TOLD ME TO ISSUE THE CLRNC AND MAINTAIN 10000 FT. BEFORE ISSUING THE CLRNC; DAY APCH CALLED TO COORDINATE FOR THE 3RD TIME ON A NON-ARTS TAGGED IFR ACFT. I TOLD DAY TO KEEP HIM COMING. I THEN RADAR IDENTED AND CLBED ACFT #2; WHO CALLED OFF OF IND. I THEN WENT BACK TO ACFT #1 AND ISSUED THE IFR CLRNC. ACFT X SAID THE CLRNC HAD BEEN BLOCKED. I REISSUED THE CLRNC; TOLD HIM TO MAINTAIN 10000 FT AND CONTACT ZID ON XXXX. ABOUT 2 MINS LATER; I HEARD THE CONFLICT ALERT SOUND. AT THE PENDS INTXN (IN INDY AIRSPACE); I SAW ACFT Z AT 10600 FT AND ACFT Z AT 10000 FT. IND ARR CTLR HAD DSNDED ACFT Z TO 6000 FT; AS IS ALLOWED BY AN LOA BTWN IND APCH AND ZID. PRIOR TO ENTERING ZID AIRSPACE; ACFT X FLT HAD CLIPPED ABOUT 1 1/2 MI OF IND ARR AIRSPACE. AND BECAUSE I HAD NOT POINTED OUT THE ACFT #1 FLT TO THE ARR CTLR; HE DID NOT SEE THE XING TFC AND DSNDED ACFT #2. FURTHERMORE; I HAVE A HABIT OF DROPPING TRACKS THAT LEAVE MY AIRSPACE; AND I PROBABLY DROPPED THE TRACK OF THE ACFT X FLT. SOME ISSUES THAT CONTRIBUTED TO MY WORKLOAD WERE; PRIOR TO ACFT X CALLING ON; DAY APCH CALLS WITH A MANUAL HDOF. I ADVISED DAY TO KEEP HIM COMING. THIS WAS THE 1ST THING IN THE BACK OF MY MIND TO KEEP AN EYE ON. THE NEXT THING WAS ACFT XX CALLED LOOKING FOR AN IFR CLRNC OFF OF HFY. SO THIS WAS ALSO IN MY MIND; FIND A CLRNC FOR HIM. ZID; ABB SECTOR CALLED FOR A POINTOUT. AND WHILE TRYING TO RESPOND TO THE ACFT X FLT; DAY CALLED 2 MORE TIMES TO COORDINATE A NON-ARTS TAGGED ACFT. ONCE I WAS ABLE TO ISSUE THE CLRNC TO ACFT X; IT HAD BEEN BLOCKED BY ACFT YY CALLING TO GET HIS IFR OFF OF ZL8. ALL THE WHILE IN THE TRACON; THE VOLUME LEVEL WAS INCREASING WITH A SHIFT CHANGE. ALSO THE DEP CTLR NEXT TO ME; WAS BECOMING VERY BUSY AND HIS VOLUME LEVEL INCREASED ALSO.